Boston Red Sox starter Tim Wakefield is baseball's most successful knuckleball pitcher of the last two decades. Wakefield was originally drafted as a position player by the Pittsburgh Pirates in the eighth round of the 1988 draft. He began pitching in the minor leagues in 1989 and spent six seasons trying to make a career of it. 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 victories, behind both Cy Young and Roger Clemens, who have 192 each, and is first all-time in innings pitched by a Red Sox pitcher, with 3006.  He is second on the Red Sox career strikeout list with 2046 and games played at 590.

Wakefield was born in Melbourne, Florida on August 2, 1966. He attended Eau Gallie High School and then attended Florida Tech. At Florida Tech, he was named the Panthers team MVP as a first baseman in his sophomore and junior years. He set single-season records with 22 home runs and 71 RBI, as well as the career home run record at 40. In 2006, his number 3 was retired by the college.  After being drafted by the Pirates, he struggled in his early professional career as a position player, but he had been experimenting with a knuckleball. Trying to fulfill his baseball ambitions by any means necessary, Wakefield made his professional debut as a pitcher in 1989. He tossed 39.2 innings in single-A with some success, striking out more than a batter per inning.  In his next three minor league seasons, Wakefield used the nature of the knuckleball to his advantage and became a major innings-eater, tossing more than six innings per start on his way to the Major Leagues. His debut with the Pittsburgh Pirates came in 1992 and his rookie season couldn't have worked out better. In 92 innings with the big league club, Wakefield had a 2.15 ERA. His second season with the club went in the opposite direction as his ERA shot up over five and he was eventually cut from the team in 1995.

The Boston Red Sox took a flier on Tim Wakefield shortly after his release. Six days after being released from the Pirates, Wakefield was signed by the Boston Red Sox. He worked with Phil and Joe Niekro, two former knuckleballers, who encouraged him to use the knuckleball as an out pitch. In Triple A Pawtucket, Wakefield went 2–1 with a 2.53 ERA.  With the Boston Red Sox rotation struggling from injuries to top of the rotation starters Roger Clemens and Aaron Sele early in the 1995 season, Wakefield was called up from Triple A, and soon proved to be their most dependable starter. He began the season with a 1.65 ERA and a 14–1 record through 17 games - 6 of which were complete games. He ended the year 16–8 with a 2.95 ERA, helping the Red Sox win the American League East division title, and capturing the Sporting News American League Comeback Player of the Year. He finished third in the AL Cy Young Award balloting.

In 1999, Boston's closer Tom Gordon was injured and manager Jimy Williams installed Wakefield as the new closer during the middle part of the season. On August 10, 1999, he joined a select group of pitchers who have struck out four batters in one inning. Because the fluttering knuckleball produces many passed balls, several knuckleballers share this honor with him. He recorded fifteen saves before Derek Lowe emerged as the new closer and Wakefield returned to the starting rotation.  Because of his success out of the bullpen, Wakefield was regularly moved from the position of relief pitcher to starter and back again over the next three seasons (2000–2002). After being moved back into the rotation in late July 2002, Wakefield became a permanent regular starter.

In the 2003 ALCS, Wakefield allowed three runs over 13 innings against the New York Yankees. He started Games One and Four of the Series against Mike Mussina and won both starts. He was also called in to pitch in extra innings of Game Seven, after the Yankees tied the game. The Red Sox had been leading 5–2 in the eighth inning. After retiring the side in order in the 10th, Wakefield gave up a home run to Aaron Boone on his first pitch of the 11th, sending the Yankees to the World Series. Wakefield apologized to fans after the game. 

In 2004, Wakefield helped the Red Sox win the ALCS against the Yankees, a best-of-seven series to advance to the World Series. The Red Sox lost the first two games of the ALCS and were losing badly in Game Three when Wakefield asked to be put into the game to save the other pitchers for the next day. He pitched 3 innings which prevented him for starting Game Four. Derek Lowe started Game Four in his place which the Red Sox ultimately won. In Game Five, Wakefield again pitched out of the bullpen and was the winning pitcher in a 14-inning game, throwing three shutout innings as the Red Sox won 5–4. The Red Sox beat the Yankees and went on to the World Series. He pitched Game One of the 2004 World Series but did not get a decision as Boston defeated the Cardinals, 11–9. The Red Sox swept the Cardinals for their first World Series title in 86 years.

In the 2005 season, Wakefield led the Red Sox pitching staff with 16 wins and a 4.15 ERA. On September 11, 2005, he set a career high in strikeouts (12) in a 1–0 complete game loss to the New York Yankees.  In 2007, he finished the season with a 17–12 record but was left off the Red Sox roster for the World Series due to an injured shoulder that had been bothering him since late September. Wakefield entered his fifteenth season with the Boston Red Sox in 2009. On April 15, 2009, a day after the Red Sox bullpen was tasked with pitching over 11 innings of relief, Wakefield told Terry Francona: "I understand the circumstances and I just wanted you to know: Whatever happens, don't take me out; let me keep going." He went on to carry a no-hitter into the eighth inning, and earned a complete-game win. At 42, this made him the oldest Red Sox pitcher to pitch a complete game, a record he would break himself in his next start when he pitched a second consecutive complete game win, this time in a seven-inning, rain-shortened game.  His success on the mound had him atop the major leagues with 10 wins at the time of the 2009 All Star selection. He was announced as an AL All-Star, making him the second-oldest first-time All-Star at 42, behind only Satchel Paige who was 45. By the All Star break, Wakefield possessed a major league-best 11–3 record.

Wakefield entered his 16th season with the Boston Red Sox in 2010. He began the year in the starting rotation until Daisuke Matsuzaka came off the disabled list. He later rejoined the rotation due to an injury to Josh Beckett. Wakefield recorded his 2000th career strikeout against Vernon Wells of the Toronto Blue Jays. He joined Jamie Moyer, Javier Vázquez, and Andy Pettitte as the only active pitchers with at least 2000 career strikeouts. On June 8, Wakefield passed Roger Clemens for the most innings pitched by a Red Sox pitcher. He went on to win that game 3-2 over the Cleveland Indians. On June 13, Wakefield joined Moyer and Pettite as the only active pitchers with 3,000 innings pitched. Against the Tampa Bay Rays, he became the oldest Red Sox pitcher ever to win a game; he is also the oldest player to appear in a game for the Red Sox at Fenway.

In 2011 Injuries to John Lackey and Daisuke Matsuzaka moved him into the starting rotation.  On May 11, 2011, Wakefield pitched in relief as the Toronto Blue Jays defeated the Red Sox 9–3 at the Rogers Centre. He became, at 44 years, 282 days, the oldest player ever to appear for the Red Sox. At the All-Star break, Wakefield had a 5-3 record with a 4.74 ERA. While pitching against the Seattle Mariners, Wakefield recorded his 2,000th strikeout in a Red Sox uniform against Mike Carp. He also recorded his 199th career win in that game.  It took Wakefield eight attempts to earn his 200th career win after his 199th, finally doing so in an 18-6 rout over the Toronto Blue Jays at Fenway Park on September 13. The victory came at a time when the Red Sox were in dire need of wins, with the Tampa Bay Rays gaining substantial ground in the race for the American League Wild Card as Boston fell four games behind the New York Yankees in the AL East division standings. Boston eventually missed the playoffs by one game, and Wakefield ended the season at 7-8 with a 5.12 ERA.

For the 2012 season, Wakefield was offered a minor league contract, with an invitation to spring training, by the Red Sox. Wakefield announced his retirement on February 17th.