Tim Wakefield
After winning No. 199 on July 24, it took Wakefield nine starts to earn his 200th win on Sept. 13. In that time the Red Sox went 24-24 and went from three games up to four games behind in the AL East. In the games he started, Wakefield had a 5.09 ERA. Obviously the Sox' record can't all be blamed on Wakefield, but it needs to be noted that while the Sox were allowing their beloved veteran to chase an individual record, the team was going into a tailspin.