I won $460 in August 1998 playing the "Cosmo's Conundrum" trivia game at Uproar, but then they changed their rules so that you didn't have to win the games to qualify for the money drawings (making it more of a lottery,) and my winnings dropped to $15 in September 1998.
I won two Joe Bob Briggs MonsterVision t-shirts in the MonsterVision caption contest, but TNT only sent me one shirt. I guess Joe Bob needed the other one for Rusty, the Mail Girl. I won an Epson digital camera in a different caption contest, and the month after I won, they changed the prize to a t-shirt. I won second prize in a Clamato humour contest judged by French Stewart, of "3rd Rock from the Sun." First prize was $10,000. Second prize was (what else?) a t-shirt.
I won 46 movie tickets from Hollywood.com, but by the time they got around to mailing them, the expiration date was only 10 days away. I couldn't go to 46 movies in 10 days. I would have died of an overdose of Milk Duds and LottaLemon.