
MrCharisma |

We had a pretty tough fight in book 1 of Carion Crown recently.
Upstairs in Harrowstone we had a difficult encounter. The Alchemist (me) and the Warpriest were unconcious and dying, and the Brawler was at 1 hit-point (3 person party, level 2). There were still enemies up, so the Brawler-player was about to run when we (the players) said: "What would your character do?"
He somehow managed to revive the Warpriest and carry the Alchemist's unconcious body out of there.
We were 1hp away from a TPK and managed to get out without any serious penalties.
We got just enough experience to level up, so we went back the next day and cleared the place out.

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I once fought off two armed opponents at once and managed to not lose. I'm not trained Law Enforcement or Military. Luckily for me they were untrained bunglers. I had about four years of combative martial arts experience at the time. One attacker drew a knife but could not deploy it before I arm-locked him. The fellow with the knife dropped it so's not to have his arm broken like a rotten twig. The other attacker delivered a few clumsy martial arts techniques to no effect (I parried with off-hand and blocked with his friend) but did not draw his [poorly] concealed weapon. The other fellow retreated and also submitted once he realized their tactical situation was hopeless. I was unscathed and did not have to injure either man. A police officer soon took custody of the two men.
That was IRL. In RPGs the GM of a 25 year duration campaign once hosted an epic 8-hour-in-meatspace game that lasted 26 combat rounds in-game. We challenged Old Man Winter to bring back the sun at the Winter Solstice, thus preventing the world from freezing in a Long Winter.
The players still reminisce about it.

Meirril |
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Hardest fight? So yeah. This is going to be a bit silly sounding but it was absolutely horrifying at the time.
This was in the Iron Gods AP. At some point we needed to kill all of the big shots in the Technic League. We managed to track one of them down while he was checking out a place we previously attacked. Each member of the Technic League is a powerful caster of some kind. He was busy performing an investigation and was surrounded by 12 of the town guard robots as bodyguards. They are called Gearsmen. We fought Gearsmen before. They were equipped with Lasers (fire damage) and Shock batons (electrical damage). We were prepared for fire damage with Resist Elemental (fire). Also our group was all ranged specialized.
The captain went down in the surprise round. High level caster never got off a single spell. All that is left is the 12 town guards. The gearsmen rolled a high initiative. All 12 of them use a Rocket Launcher and wouldn't you know it, the entire party is standing in an ally so of course we're close enough that the entire party is in the AoE for the 12 attacks.
We're basically immune to the fire portion of the attacks. We aren't so immune to the 6d6 x 12 physical parts of the attacks. Most of us made the saving throws vs all 12 rockets. The DC is a bit low. But half is still 36d6 damage!!! The Alchemist and Cleric were almost dead. My fighter was at less than half hp. The ranger and gunslinger...have evasion. They are fine. Bastards. The two buildings next to us are now ruins.
We've fought things with rocket launchers before. We have 2 rocket launchers. We know rocket launchers are 5 shot disposable weapons. 5 shots. The 3 of us without evasion run for our lives and find cover from the rocket barrage. The ranger and gunslinger kill off the 12 gearsmen in 3 rounds so we have a whole lot of 2 shot rocket launchers left at the end. But seriously we almost lost 3 characters to low level shlubs because they had 12 weapons we couldn't avoid 3d6 damage from each.

Yqatuba |

I once fought off two armed opponents at once and managed to not lose. I'm not trained Law Enforcement or Military. Luckily for me they were untrained bunglers. I had about four years of combative martial arts experience at the time. One attacker drew a knife but could not deploy it before I arm-locked him. The fellow with the knife dropped it so's not to have his arm broken like a rotten twig. The other attacker delivered a few clumsy martial arts techniques to no effect (I parried with off-hand and blocked with his friend) but did not draw his [poorly] concealed weapon. The other fellow retreated and also submitted once he realized their tactical situation was hopeless. I was unscathed and did not have to injure either man. A police officer soon took custody of the two men.
Had a feeling someone would list a real life fight. That said, that's pretty awesome.

Volkard Abendroth |

I had sever fights in Rapan Athuk where my magus was the sole survivor.
On one of them, we faced a stone golem (closest analogy) at 3rd level. Ate the rest of the party, but it could only move 30'/round. Between Acid Splash and Grease I finally wore it down.
In another room, someone did something very stupid and summoned a demon when we were 4th level. I waited a couple of levels and went back in solo, when it was still CR+6.
In a third encounter, I surrendered without drawing my sword while the rest of the party attacked. They died in 2 rounds; my magus was fully in vested in diplomacy and made new friends while everyone else rerolled.
Rapan Athuk is a very, very bad place. I hit it with my axe is not always the best answer.

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I just went into #9-25 (levels 12-15) this afternoon; four players at high tier. We also opted to play hard mode when the judge asked us, under the theory that it would be more exciting!
Yeesh!
The first encounter wasn't too bad, but the second was frightfull. We won, but had to withdraw from the adventure. We got 1 XP, 0 prestige and 1/4 of the available loot.
The Huge Undead creature was destroyed. The Huge Demon had about 2/3 of his hit points left, but teleported out to report on the experimental undead's combat performance as per orders...
The 5337 gp loot was insufficient to pay for the Greater Restoration that got my 5 levels back (5910), and the Inquisitor was way worse off.
To quote Frank Gorshin from the 60's Batman tv show, "Golly Batman, that smarts!"

Matthew Downie |
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Luckily for me they were untrained bunglers. I had about four years of combative martial arts experience at the time. One attacker drew a knife but could not deploy it before I arm-locked him. The fellow with the knife dropped it so's not to have his arm broken like a rotten twig. The other attacker delivered a few clumsy martial arts techniques to no effect (I parried with off-hand and blocked with his friend) but did not draw his [poorly] concealed weapon. The other fellow retreated and also submitted once he realized their tactical situation was hopeless.
Sounds like they were a badly under-CRed encounter, despite their action economy advantage.

JiaYou |
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My first day DMing Kingmaker came within one action of a TPK. My players decided to go after Kressle immediately despite my hints that they maybe should settle at the Trading Post and do some other things first. I played things more or less straight: bandits who know the woods absolutely could appear on either side of the party, which was in fairly loose formation. Fighting mostly single-combat (Druid, Cleric and Gunslinger) against the bandits meant they were taking damage, especially against Kressle as I had two humans and a Half-orc. The humans went down first, and it was just the Half-orc Druid and her companion against Kressle. Kressle takes the Druid down to something like negative 4, and the party is thinking that that was it, and I was thinking that too. Thankfully, I remembered Orc Ferocity, Kressle missed the attack of opportunity against the Druid casting Cure Light Wounds, which got her to exactly 1 HP, and the animal companion (legitimately, no dice fudging) took Kressle out the next round. The Druid then ran to the nearest tree, cast Goodberry, and generated enough berries to stabilize both characters and bring the Cleric back to zero, who then channeled the party back to not-an-absolute wreck.
For my first "real" session DMing, it was friggin epic.

Valandil Ancalime |

Big/last encounter from

Anguish |
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Did you ever have only one player surviving?
Wrath of the Righteous. Party of three at 13th level, 5 tiers. Didn't realize how outclassed we were, challenged a CR25 person whose attitude we didn't like.
We got a number of exceptionally lucky rolls that lead us to believe this was do-able, and got a massive head-start towards winning the fight, and neutralized many of the opponent's best moves before it got to go, without realizing what we had done.
Ended with one PC below 0hp but not dead, and the other two with somewhere between 1 and 5 hp each, and a bunch of negative conditions.
But we won, purely because the dice blessed us. It wasn't even "mythic is broken"... it wasn't a fight we would have won 19 times out of 20.
So very massively memorable because we staggered out of the creature's lair completely spent but pretending to be unhurt.

Yuugasa |
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So there I was, in a bar with a group of rough bikers that had just insulted a pretty lady I liked. These guys were beefy and strong, and not afraid to use violence, just the other day they had broken all of some dudes arms and legs.
I may be 5'4" and 108 pounds and this was real life, where any one of these sleezy guys could snap me in half like a twig, but I stood up and got in the lead bikers face.
"Say that again, I dare you." I told him in a cold tone.
He stood, towering over me, and drew a twelve inch blade. A wicked grin crossed his face but before he could respond I kicked him in the junk hard. He toppled with a groan as his eight buddies stood.
They were tough, but I am fast and well trained in martial arts, and within a minute they were all rolling on the ground while I stood unharmed. I turned to my hot friend, who looked like Jessica Alba in the first season of that old show Dark Angel, but like 50 times hotter.
"My Hero!" She said and we started making out. Real life can be pretty cool sometimes.
Then one thug, shakily getting to his feet, drew a gun and fired at me, I caught the bullet using the ancient art of-
"Come on man, it's your turn." Said my twelve year old cousin, interrupting my daydream.
He was a little punk, and a bad GM.
"Look kid, I'm only level two and you're plopping a Great Wyrm Red Dragon and a Terrasque on me all at once, sure its a ridiculously hard fight, but maybe go with something of a more appropriate CR?"
"Fine." He said, exasperated at all my complaining. "You win."

Slim Jim |

I don't know about the hardest fight, but I definitely remember the DULLEST adventure I've ever been on and won. Once upon a time, there was an incredibly awfully-designed PFS module with a basilisk or a cockatrice (I forget which) in an early fight at a low-level tier. My cleric rolled a 2 fort-save, and I, the player, enjoy the next three IRL hours not doing a damned thing while the rest of the party spent a week IGT hauling a heavy-ass statue of me over all creation while the GM kept teasing ways to see if they'd drop it.
(If anybody remember the name of that stupid mod, *please* do go ahead and spoil it right here, because it really was a putrid piece of garbage that I'll hate forever.)

ShroudedInLight |
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I dropped my players into a 1v1 boss fight designed to force them into a small diversion from the main plot so I could have a bit more design time. The concept was a band of Orc raiders finds the party, forces their strongest warrior to fight their chief, and then drags the party back to their village as captives. Ye standard wake up naked in a dungeon with a side of being forced to fight as fodder on the orc front lines.
Their chief was a full geared PC statted Antipaladin with 4 levels on them, the 1v1 was meant to be a shoo-in. The party, expecting death at the hands of the 20 orc warband and their badass chief sends in the Summoner's Eidolon. Monty, a lovable hug-golem, proceeded to lose initiative but the Orc Warboss missed his first swing because of a nat 1. Monty proceeds to double Slam, rolling 2 different nat 20s but only manages to confirm one of them as a crit. The boss is now down below half HP. I intended to have the warboss play around a bit, but getting hit twice changed that plan. The boss lands a hit with his flaming conductive greatsword, channeling negative energy thanks to antipaladin, further negative energy damage with channel smite, power attack, and reduces Monty to 8 HP from full. Worth noting, I rolled below average there, if I rolled above average Monty would have been banished back to his box in the astral plane. Still, there is no way Monty's two slams can deal enough damage to finish off the warboss even if lands both. Except he not only lands both hits again but rolls a 3rd freaking natural 20. Confirms the crit and drops the Warboss into the negatives. I'm stunned since this is the second time in 2 months that the party has managed to absolutely flummox my plans. The set-up doesn't work without the warleader. This wasn't even a case of my boss getting out action economized like the last time they messed up the story, this was some absurd 1/5000 chance of a commoner taking down a dragon with a sling. The rolls almost had to be exactly the way they fell, with a nat 1, 3 natural 20s, two seperate crit confirms that only happen on a 15 or better, at least 1 max damage crit, and a series of below damage d6s.
The remaining orc war-boys fall silent for a few moments as I take a quick bathroom break to assemble some thoughts. Well, the summoner wanted to swap characters anyway so this was as good a time as any. The Orc's grabbed Monty and his summoner, declared them the new chief, and rode off into the sunset with them. Overall, everyone thought it was a very appropriate end to the character arc.

Ryze Kuja |

Hardest fight I've ever been in was in a homebrew campaign; it was a fight with an "Ice Queen" Vampire and her Anti-paladin husband. Our group was a Warpriest, Investigator, Paladin, and Psionic Wilder (me). The Vampire summoned a bunch of Ice Fey and the Anti-paladin had serious "backstory beef" with the Warpriest, so he teleports himself and our Warpriest to a different dimension to fight in 1v1, leaving myself, the Investigator, and the Paladin alone with the "Ice Queen" and all her Fey. The Ice Queen Vampire dominated our Paladin, who then proceeded to turn my face into cat food-- even rolled a nat 20 on me. The Investigator basically had to kill the Vampire by himself while I had to kill the Fey and unsuccessfully dodge the Paladin (I tried to dispel him twice and failed both times-- it was awful).
In the end, my Psicrystal Falcon familiar was dead, I was -12 and dying, the Investigator was still up with like 3HP, and the Warpriest barely killed the Anti-paladin in a 1v1. But ironically, the Paladin didn't take very much damage :P

Tim Emrick |
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When I was first teaching my kids Pathfinder, I created an adventure for their brand-new 1st-level characters in which they defended a farm from a handful of goblin bandits. That part went fairly easily, but then they had to track the fleeing survivors back to their lair, where their boss was. The leader was (IIRC) a fighter 1/rogue 1, and managed to take down a couple PCs within a couple rounds because they didn't kill his flank-buddy minion fast enough.
Soon it was down to just two left standing: the boss and my son's sorcerer, who was out of spells except for cantrips. The combat then became a running fight through the cave, with the sorcerer plinking the boss with acid splash, and the boss missing every single attack roll. The sorcerer's luck held out just long enough to take the boss down, then he ran back to his friends to administer first aid. Miraculously, no PCs died, but the sorcerer had to stand guard over his friends for a day or two until they healed enough to wake up and limp home.

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Not sure it counts as winning, but I had a group of 5 level 4 characters follow up a rumour, and found themselves facing a (CR7) spectre in the basement of a house, in the middle of the game day. The party healer (a warpriest) successfully identified the creature, and chose to lie to the group, saying it was a shadow. After a couple of guys got hit with the 2-negative-level touches, and the group doing very little to it, they finally decided to bug out. After a bit of maneuvering over a couple of rounds, everyone was ready to leave, but by now everybody had 2 negative levels (yes, I was being nice). The Warpriest could have withdrawn, but decided to take one for the team to get everyone else out, and purposely drew an AoO. The spectre rolled a nat 1 on its attack, the warpriest breathed a sigh of relief, and walked into the sunshine. All of the other PCs quickly stampeded past it out the door, and into the safety of the sunlight, with nobody actually dead, or rising as a baby spectre.

Tarik Blackhands |
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Not Pathfinder but Dark Heresy (Aka Warhammer 40k).
I am playing a low rank (read: semi-incompetent) hospitaller (Also read: largely non-combat focused) and together with fellow battle sister are trying to escape a field hospital being overrun by mutants.
After clearing through some chaff we run into a big mutant that, by random mutation was a wyrd. We clear out his followers and his turn rolls by where he tries to use a psychic power. He gets a 9 meaning he causes warp phenomena. He gets a 75+ on the d100 roll meaning he invokes Perils of the Warp. He gets a...93-99 I believe meaning he turns into an Unbound Daemonhost.
To those not in the know, an Unbound Daemonhost are hideously potent psykers and are not to be trifled with by high level characters, to say nothing of a bunch of low rank losers like myself. Fear naturally kicks in instantly with myself wretching on the floor and my partner spending a fate point to autopass. She manages to stitch it a few times with her boltgun before getting telekinetically slammed into the wall and KOed instantly roughly the same time I come back to my senses and I assess the situation.
There's no real escape for me, my piddly autogun isn't going to scratch the host's hide, and even then my combat stats suck. I choose the only option left to me which is to dive to the ground and grab the fallen bolter (that I'm not proficient in) and go for a proper death or glory attack. Now despite using the semiautomatic setting and the daemonhost being point-blank, I'm at basically a coinflip to hit it (35 base+30+10 range/semi -20 non-proficient) but hey, go out swinging I say.
Swinging I did. All three shots land, two of the damage rolls explode (10 again basically), one of which explodes twice, and in the end there's a pile of red mist that was formally a daemonhost and one utterly befuddled medic. From there the escape succeeds in a fairly mundane manner.
The Lesson: Even when things seem most hopeless by dice screwage, the Emperor Protects.
And no, there wasn't any cheating or fudging involved, all rolls were in roll20 and open to plain view.

Bjørn Røyrvik |
A couple.
One was a perfectly normal encounter in a dungeon, not a boss encounter or anything. The PCs just waltzed right into a dragon lair, with the dragon having one round to prepare. The dragon snatched, flew off and killed two, over the course of five rounds and reduced the third to negatives before being killed. This was at a level where the PCs (and players) should have handled this easily.
In the appropriately titled "Death's Ride" adventure we had what was technically a TPK, but I fudged a bit and had the granduncle of one of the PCs come in and (sorta) save the day - by which I mean he killed the baddies, abducted his grandniece, and left the others to die.
I still get dirty looks when I mention this adventure and some of the monsters therein.
"Talons of the Night" had everyone left standing by the end (even if there were some deaths during the fight), but the PCs did expend five or six Wishes and two Miracles to break even against a severely nerfed Immortal.
When I wanted a wee break from GMing my gf ran RHoD for us, set contemporarily with our normal campaign. We failed, so I took over, buffed Tiamat a little and let her loose on the 16th level PCs from our normal campaign. There were six deaths divided among four PCs, but they did manage to take her down.

Archimedes The Great |

The toughest encounter that I've ever had was one in which the DM misunderstood the mechanics of two....very powerful spells.
Disintegrate, where the RAY was treated as a LINE... So 3 people were being hit at once.
And reverse gravity where 3D space in Cubic feet was treated as 2D square feet... so four people were being affected at once.
Surprisingly only 1 death...

Yqatuba |

The toughest encounter that I've ever had was one in which the DM misunderstood the mechanics of two....very powerful spells.
Disintegrate, where the RAY was treated as a LINE... So 3 people were being hit at once.
And reverse gravity where 3D space in Cubic feet was treated as 2D square feet... so four people were being affected at once.
Surprisingly only 1 death...
I don't really understand the thing for reverse gravity. Are you saying he made the area it effects way bigger than it should have been?

doomman47 |
We had a fight that was suppose to be really difficult 4 cr equivalent encounters but we countered that really well, so it was fairly easy hardest fight that should have been winnable was against a bird who was huge sized and had a few templates stacked on it, one party member didn't show for that session and we ended up tpking.

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I don't know about the hardest fight, but I definitely remember the DULLEST adventure I've ever been on and won. Once upon a time, there was an incredibly awfully-designed PFS module with a basilisk or a cockatrice (I forget which) in an early fight at a low-level tier. My cleric rolled a 2 fort-save, and I, the player, enjoy the next three IRL hours not doing a damned thing while the rest of the party spent a week IGT hauling a heavy-ass statue of me over all creation while the GM kept teasing ways to see if they'd drop it.
(If anybody remember the name of that stupid mod, *please* do go ahead and spoil it right here, because it really was a putrid piece of garbage that I'll hate forever.)
That might be The Veteran's Vault.

Archimedes The Great |

I don't really understand the thing for reverse gravity. Are you saying he made the area it effects way bigger than it should have been?
Reverse gravity targets a 10 foot cubic area/level. This is different than a 10 ft square area/level in the sense that if you want want to make somebody fall all the way up and slam into a 150 foot ceiling, then you need to affect 15 (10 cubic foot area) in a column to make the gravitational force in that whole column reverse.
My GM was applying the reverse gravity to just area and ruled that the gravity in that area was reversed all the way up. So therefore our entire party with exception of the feather falling witch (spread out in a massive room) all slammed up 150 feet into the ceiling and then fell 150 feet the next round.