So close!
OK, based on your screenshots, you've got 3 relevant prizes configured. One is for a bounty on a specific player (Player 2). The other two are awarded to random players. The reason you're not seeing the event fired is the event's Conditions. The Conditions say "isBountyPrize", meaning only fire when the prize being awarded is a bounty on another player. Since the trigger is "A random player is chosen for a prize", the event could be triggered by either a prize being awarded to a random player (like your two prizes) OR a prize being awarded as a result of busting out a random player (a bounty on a random player). The Conditions restrict it to the second (a bounty on a random player). But you don't have any prizes that are awarded as a bounty on a random player. Thus, no firing of the event.
Remove the conditions (leave the Conditions blank) and this should work for when one of those 2 prizes is awarded to a random player.
Two more small notes:
1) You'll probably want to clean up the message that is displayed. Remove the extra < in front of <hitman>. And put spaces in between the words and the tokens, or else everything in the message will run together:
<prizepoints> TO <hitman> FOR KNOCKING <randomname>2) I see that the
Cheat Sheet button has text on it.
(I'm referring of course to this:
http://www.thetournamentdirector.net/forums/index.php?topic=4641.msg19581#msg19581)