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Give a thousand gnolls +2 Strength composite longbows, Deadly Aim, and a fair bit of distance. Maybe have them surrounding the fellow.
1000 attacks = 50 hits (including about two crits).
We'll give the fighter DR 5. The gnolls are dealing 1d8+4 damage per hit. His DR only blocks all the damage on minimum--six hits will deal nothing (rounding down because I rounded down on the 2.5 crits).
So that's approximately 188 damage in a single round. Probably more. Assuming the fighter has a 20 Constitution, he still has about 20 hit points left. He can fire a ranged weapon and kill a dozen or so.
Then he dies.
The solution is an army of archer gnolls. They pour so many arrows upon the fighter, so many sticking into shield, armour, that he goes to heavy encumberance from the sheer weight. Then they continue to skirmish, flee and harry the fighter, lay out caltrops, never engage.
I think 300-350 gnolls could do it. They need about 30 lbs in arrows each, longbow, no melee, 20 lbs in caltrops, relatively flat ground, or it could also be done in rocky terrain to annoy and escape the fighter, and roll rocks onto his head.
Lol, this is fun.
Does grapple succeed on a natural 20? If so, "all" you need is for 20 gnoll to roll a 20 on his grapple check, for the fighter to roll a 1 on his grapple check to break free, and then for the gnoll to roll another 20 to pin him. Then you've got a coup de grace possible. The odds of a 20, followed by a 1, followed by a 20 are pretty darn slim, though.
Any method that relies on dealing damage, in my own opinion, stands no chance against a fighter with DR and a ring of regeneration.
This is the most probable means to kill a fighter on endless flat terrain, I believe. Relying on 3 trick rolls. However, if the terrain is not flat, then this can change drastically. Add a chasm and then the gnolls can attempt to bull rush the fighter into it.
This is all assuming a natural 20 on a combat maneuver roll is auto-success, which I'm not sure of. If it's not, then a properly equipped fighter can kill infinite gnolls until you start factoring in fatigue with some homebrew rules.
Wow, I did not expect to be ninja'd in that way. I think my post outlined that your idea is a perfectly viable tactic. It'll take a while, but it'll succeed eventually.
Yes, a natural 20 auto-succeeds a CM check.
Oooooohh, they could all try to called shot to the heart him in hopes of a crit to deal con bleed. That could reduce the fight to a matter of minutes, unless the Ring of Regen stops that...
Actually, seems like pinned doesn't mean helpless in Pathfinder.
So this won't work.
As for the odds of everyone in a round doing criticals to beat SR and regen, you'd need it to happen many rounds in a row. I'm a bit fuzzy in recalling my statistics classes, but I'm pretty sure your odds of winning the lottery are better.
As for the archers, +2 strength composite longbows and deadly aim aren't stock. XD
Fine. Have 24,000 STOCK gnolls allow themselves to be killed by a 24,001st STOCK gnoll. Assuming one coup de grace per round, this takes only 2,400 minutes. That's not even two days.
You now have a level 20 gnoll barbarian. With two racial hit dice.
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I would think the smell from say, 100 gnolls would be enough to make any sane level 20 fighter fall upon his vorpal sword to avoid the stench.
10, if they ran all the way to greet the fighter.
1 if its a female in heat and has our noble fighter in a bear hug.
1 Gnoll.
Yep. 1.