When I was in school, I gave a guy 75 points going to 100 in straight pool and beat him 100 to 74.
I also was playing 8-ball, letting this guy pick his group after the break and take all of his balls off the table. That is an old sucker bet, similar to what Larry said above. I would win easily since his balls were all off the table. After a while we adjusted to where I would play one and stop, meaning that I could only run one ball at a time and then I had to play safe. That at least guaranteed him one clear shot at the 8-ball each rack since I had to play safe after making my last ball. He couldn't win at that either so I adjusted further by letting him call 3 pockets for the 8-ball each time he shot.
I was also playing 9-ball against two other guys in a ring game format, but we were playing 1-foul ball in hand rules, like regular 9-ball. The catch was that the two guys were playing as a team, so one of them would scratch and the next would take ball in hand. They were so bad that they couldn't win that way until they figured out that the first guy would just shoot at the 9-ball and hang it and the second guy would take ball in hand and play the combination. I ended up breaking even on that bet.
I also spotted some girl the 6-out, race to 7, loser pays for dinner. I lost on purpose, got a date out of it, and now we have been married for 7 years. The only question I have now is "who was hustling who???"
Andy