| DM_Blake |
This ability goes on a ranger, so in order for a wolf to use it he would need 5 levels of Ranger (Skirmisher). I suppose if you are a ranger and you have a wolf and some way to apply this trick to your wolf, then your wolf can use it.
If a wolf has access to this trick, then each time it hits with a bite it can make two trip attempts. I would use its natural trip (the one every wolf has from its Trip ability) first because that one does not provoke an AoO. If that fails, then it would use the second trip (from Upending Strike) which does provoke an AoO.