On June 4, Crisp was the center of controversy in a game against the Tampa Bay Rays. While Crisp was trying to steal second base in the bottom of the sixth inning, Rays shortstop Jason Bartlett purposely placed his knee in front of the bag in an attempt to prevent Crisp from stealing the base. Crisp stole the base, but was not happy with this. On base again in the bottom of the eighth inning, he attempted another steal, this time taking out second baseman Akinori Iwamura on a hard slide. His slide was controversial and catalyzed the "payback pitch" the following game. During a pitching change in that inning, Rays manager Joe Maddon and Crisp argued, with Crisp in the dugout and Maddon on the pitching mound. After the game, Crisp said that he thought Bartlett would cover the bag, instead he (Bartlett) chose to tell Iwamura to take the throw in the eighth inning. Crisp described Bartlett's knee in front of the bag as a "Dirty" play. During the next game, with Crisp at bat in the bottom of the second, with the inning with the Sox up 3–1, Rays starter James Shields hit him on the thigh on the second pitch. Crisp charged the mound and first dodged a punch from Shields, and then threw a glancing punch at Shields, which set off a bench-clearing brawl. Crisp, Jonny Gomes, and Shields were ejected from the game. Major League Baseball suspended Crisp for seven games due to his actions in the brawl. Upon appeal, the suspension was reduced to five games, which he had served as of June 28, 2008. In Game 5 of the ALCS, Crisp had a game-tying hit in the bottom of the eighth inning to cap Boston's seven-run comeback. Boston would go on to win the game 8–7 with a walk-off single in the ninth inning by J. D. Drew, but eventually lost the series in seven games.