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Even if you are using a weapon's reach, you aren't using it in a way that the weapon was designed (tripping with the haft, hilt, or crossguard, not the slashy/piercy/smacky part). So I am highly doubtful that a bleed effect would go off after succesfuly shoving/tripping/sand tossing(to blind)/repositioning a creature.
I don't think it's intended:
When the result of the die roll to make an attack is a natural 20 (that is, the die actually shows a 20), this is known as a critical threat (although some weapons can score a critical threat on a roll of less than 20). If a critical threat is scored, nother attack roll is made, using the same modifiers as the original attack roll. If this second attack roll is equal to or greater than the target’s AC, the hit becomes a critical hit, dealing additional damage.
Critical Hits: When you make an attack roll and get a natural 20 (the d20 shows 20), you hit regardless of your target’s Armor Class, and you have scored a “threat,” meaning the hit might be a critical hit (or “crit”).
Both sections point to AC (the first only at confirmation, but still). CMD is not mentioned. Rolling a 20 at a maneuver is described as following:
Rolling a natural 20 while attempting a combat maneuver is always a success (except when attempting to escape from bonds), while rolling a natural 1 is always a failure.
So appearantly there is no critical hit. Which is probably for the better - it would favor weapons with high crit range even more...
Finally, Pushing Assault gets a special effect on a critical hit:
If you score a critical hit, you can instead push the target 10 feet directly away from you.
Since it's called out in the feat description, it's an exception.