2) You can use them both on the same target if he triggers both at two points during the round, but they can't happen at the same time (they have completely different triggers). This would be highly unlikely to happen, however.
Unless you have the Mobile Challenge feat. Then, if the marked enemy tries to shift away and charge your ally, you hit it with Combat Challenge when it shifts, and shift after it, then when it tries to charge, you take your OA and stop it cold if you hit again due to Combat Superiority.
Easy thing that'd trigger both: Marked enemy makes a Ranged Attack. If you happen to have an Enchanter in the group this'll happen a lot.
Easy thing that'd trigger both: Marked enemy makes a Ranged Attack. If you happen to have an Enchanter in the group this'll happen a lot.