Did Tim Wakefield ever win a World Series?
Yes, with the Pirates
Yes, with the Red Sox
No, he never won
He won with both Pirates and Red Sox
Answer
Yes, Tim Wakefield did win a World Series with the Red Sox. He won two World Series with the Red Sox, in 2004 and 2007. He was a key part of the team's pitching rotation during those two seasons, and he helped the team win both championships.
Knuckleball Extraordinaire: The Tim Wakefield Quiz
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