*You and a rival are both invited by your boss to visit his health club and play a few rounds of golf or tennis. Obviously the idea here is to lose convingly enough to boost the boss's ego, while showing up your rival. This could be a mini-game, (in which the object of the game is to challenge your boss and beat your rival but not play well enough to beat your boss), but a simpler idea would be to slip your rival some kind of perfromance enhancing substance, or special sports equipment, so they inadvertantly beat the boss really badly in the game, humiliating them boss and making him angry at your rival.
This could be an interesting blind information game if both you and your rival have to choose beforehand how well you will play (as well as what sabotage to do either to increase or decrease your opponent's ability). To do this you can have the boss challenge each of one individually without the other watching, then he watches both of you play each other. you can't play better in the second match as the boss will then know you went easy on him and ruin his trust in you. The object then is to lose as badly as possible to the boss for maximum boss ego boost, but still beat your rival when going head-to-head so you're seen as second best, not a complete loser.
Presented as a logic puzzle it would be:
Choose a number between 1 and 50 as your start skill and a number between -10 and 10 as a modifier for your opponent. Reveal both numbers simultaneously. The winner is the closest to 25 without going over. Score = amount under 25 you chose minus 10 if you were the lowest number, or minus 25 if you go over 25.