Wakefield began his pitching career with the Pittsburgh Pirates, but is most remembered for his 17-year tenure with the Boston Red Sox, starting in 1995 and ending with his retirement in 2012 as the longest-serving player on the team. Wakefield, at the time of his retirement, was the oldest active player in the majors.

Known for his signature knuckleball, Wakefield won his 200th career game on September 13, 2011 against the Toronto Blue Jays, and is third on the Boston Red Sox with 186 team victories, behind both Cy Young and Roger Clemens. He is second in all-time wins at Fenway Park with 97, behind Roger Clemens' 100, and is first all-time in innings pitched by a Red Sox pitcher, with 3,006, having surpassed Roger Clemens' total of 2,777 on June 8, 2010.

This Rawlings official National League baseball was signed un blue by Wakefield and includes a Great Moments COA.