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Looking back at Tim Wakefield’s best moments with the Red Sox

Dan Shaughnessy remembers Tim Wakefield
WATCH: Sports columnist Dan Shaughnessy joins Boston Globe Today to celebrate the life of Tim Wakefield.

Tim Wakefield, the knuckleballer who won two World Series titles with the Red Sox, died Sunday at the age of 57 after a brief battle with an aggressive form of brain cancer.

Wakefield won 200 games over 19 years in the majors, including 186 wins during his 17-year tenure with the Red Sox.

Let’s take a look back at some of Wakefield’s most memorable moments in Boston.

Sept. 22, 1995: Comeback Player of the Year — After spending most of 1994 with the Pirates’ Triple A affiliate, Wakefield was released by Pittsburgh in early 1995 and signed by the Red Sox just six days later, reporting to Triple A Pawtucket.

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Injuries in the rotation gave Wakefield an early chance with the big-league club, and he never looked back. Wakefield finished the year 16-8 with a 2.95 ERA, becoming the Sox’ most dependable starter in unlikely fashion, and was named American League Comeback Player of the Year by Sporting News.

Wakefield’s debut season in Boston was good enough to earn him third place in AL Cy Young voting.

Aug. 10, 1999: A four-strikeout inning — With regular closer Tom Gordon injured, Wakefield took up the role anchoring the Boston bullpen and accomplished a rare feat: striking out four batters in one inning.

Called upon to close out the Royals, Wakefield punched out the first two batters he faced, then got future teammate Johnny Damon swinging for his third strikeout of the inning. A passed ball saw Damon reach despite fanning, and Wakefield had to strike out a fourth batter to finish the game.

Oct. 16, 2004: Taking one for the team — Wakefield was revered for his selflessness off the field, as one of the most charitable players in the league during his career and after his retirement. That selflessness came out on the field most notably during the famous 2004 ALCS against the Yankees, when Wakefield entered a Game 3 blowout loss to the Yankees to handle mop-up duty, tossing 3 ⅓ innings and giving up his Game 4 start.

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Wakefield set his ego aside and helped save the rest of the Sox pitching staff — particularly the bullpen — which proved crucial with Games 4 and 5 each requiring extra innings as part of the Sox’ legendary comeback from 3-0 down in the series.

“My biggest challenge wasn’t worrying about the final score of Game 3. It was how we were going to be positioned for Game 4,” said then-Sox manager Terry Francona. “So when Wake showed up in his spikes and volunteered to eat up innings in Game 3 — and sacrifice his Game 4 start — it immediately gave me renewed energy to working toward tomorrow.”

Oct. 23, 2004: A World Series start — Twelve years into his major-league career, Wakefield’s ALCS selflessness was rewarded with his first World Series start in Game 1. Wakefield came away with a no-decision, but the Red Sox won the series opener and beat the Cardinals in a sweep, the club’s first championship in 86 years.

Wakefield’s numbers weren’t impressive in that 2004 run, but his contributions to the curse-breaking title will never be forgotten.

Sept. 11, 2005: A gem in the Bronx — Wakefield’s career will always be linked to the Yankees, for reasons good and bad, but he put in one of the best performances of his career at Yankee Stadium in 2005, fanning a career-high 12 batters and allowing just one run in a complete game performance in a crucial AL East showdown.

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Despite Wakefield’s heroics, the Sox couldn’t get it done; future Hall of Famers Randy Johnson and Mariano Rivera combined for a shutout, and Wakefield took the loss in a 1-0 defeat.

Oct. 28, 2007: Championship No. 2 — Wakefield didn’t pitch in the 2007 World Series because of a shoulder injury, but he earned his second ring when the Sox swept the Rockies to win their second championship in four years.

The knuckleballer won 17 games that season, second only to Josh Beckett.

April 15, 2009: More selfless brilliance — With the Boston bullpen stretched to its limits having thrown 11 combined innings the previous day, Wakefield knew he had to go deep into his start against the Athletics.

“I understand the circumstances and I just wanted you to know: Whatever happens, don’t take me out,” Wakefield told Francona. “Let me keep going.”

Wakefield rode his knuckleball to one of the best starts of his career, taking a no-hitter into the eighth and going the distance at 42 years old to become the oldest Sox starter to throw a complete game.

July 3, 2009: A Sox record and an All-Star nod — Wakefield became the Red Sox’ all-time leader in games started just before the All-Star break in 2009, surpassing Roger Clemens, taking the ball to open the game for the 383rd time.

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Wakefield had a bit of a career renaissance in 2009, going 11-3 in the first half to earn his first career All-Star selection. At 42 years old, that made him the second-oldest player to be named to his first All-Star Game, behind only 45-year-old Satchel Paige.

Oct. 28, 2010: Roberto Clemente Award — Long-admired for his philanthropic work, Wakefield was finally honored (after eight nominations) with the Robert Clemente Award, given annually to the MLB player who “best exemplifies the game of baseball, sportsmanship, community involvement, and the individual’s contribution to his team.”

Sept. 13, 2011: Win No. 200 — The 2011 season saw plenty of milestones for the knuckleballer, becoming the oldest player in Red Sox history (turning 45 before season’s end), recording his 2000th strikeout with the club, and, most notably, claiming his 200th career win.

It took eight tries, but Wakefield finally broke through in a blowout win over the Rays in September. He became the 89th pitcher to hit the 200-win milestone, and the fifth to hit the mark while pitching for the Red Sox.

It was the 186th and final win of his time with the Red Sox.

Tim Wakefield has champagne poured on him after recording his 200th career win in Boston's 18-6 victory over the Blue Jays on Sept. 13, 2011.Winslow Townson

Feb. 18, 2012: Calling it a career — Wakefield finally put his knuckleball away for good ahead of the 2012 season, announcing his retirement just before spring training.

He retired as the Sox’ all-time leader in games started (430) and innings pitched (3006), and finished six wins shy of Cy Young and Roger Clemens (192) for the organization’s win record.

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Amin Touri can be reached at amin.touri@globe.com.