Looking back at Tim Wakefield’s most notable games against the Yankees

Tim Wakefield, the reliable knuckleball pitcher for the Red Sox, who made a powerful comeback after surrendering a crucial home run to the Yankees in the 2003 playoffs, ultimately aiding Boston in winning the World Series and breaking their famous curse in 2004. He passed away on October 1, 2023, at the age of 57 after battling an aggressive form of brain cancer.

Tim Wakefield achieved 200 wins in his 19-year career. He spent 17 years with the Red Sox and won 186 games there. Against the Yankees in regular season games, he had a record of 9 wins, 14 losses, 1 save, 3 holds, and 1 blown save in 49 games. In postseason games against the Yankees, he played 4 times and had 1 win with a 3.79 ERA in 12 innings. He got his only postseason win against them in Game 1 of the 2003 ALCS.

Let’s explore some of the most memorable moments when Tim Wakefield played against the Yankees.

October 8, 2003, Tim Wakefield powers Red Sox over Yankees

It was the 2003 ALCS Game 1. Tim Wakefield pitched six innings and allowed only two runs as the Red Sox won the ALCS opener against the Yankees with a score of 5-2.

October 13, 2003, Tim Wakefield dominates Yankees

In the 2003 ALCS Game 4, Boston was behind two games to one before this game, so they needed a strong performance from Tim Wakefield to tie the LCS. He delivered just that, allowing only one run in seven innings and striking out eight. Boston won the game, 3-2.

October 16, 2003, Aaron Boone makes history

In the Pedro Martinez vs. Roger Clemens game, Aaron Boone and Tim Wakefield ram away with the spotlight. Martinez allowed a ground-rule double to Matsui and a bloop double to Posada, resulting in a tied game that went into extra innings. Mariano Rivera entered the game in the ninth inning and pitched three scoreless innings.

Tim Wakefield pitched a scoreless tenth inning for Boston. In the bottom of the 11th, he faced Aaron Boone, who came in as a pinch-runner earlier. On his first pitch of the inning, Boone hit a walk-off home run into the left-field seats. Fox Sports showed a series of images afterward: tears in the eyes of Aaron’s brother, Seattle Mariners infielder Bret Boone (who was the guest announcer), ALCS MVP Rivera running to the mound and joyfully collapsing on it, Boone jumping on home plate, and Rivera being carried off on his teammates’ shoulders.

April 16, 2004, Tim Wakefield reemerges

Six months after that memorable October night, 37-year-old Tim Wakefield was chosen by new manager Terry Francona to be the starting pitcher for the first 2004 matchup between the Red Sox and the Yankees. It was a Friday night game at Fenway Park. The Yankees had already played two games against the Tampa Bay Devil Rays at the Tokyo Dome in Japan to start the season, and they came to Boston with a 5-4 record. Meanwhile, the Red Sox had a record of 4-4.

Tim Wakefield was known for his knuckleball pitching style, and he had mostly been a starting pitcher for the Red Sox. He had even won 11 or more games for Boston six times, including an 11-7 record in 2003. This game in 2004 was only his second start of the season. It was a cold night, with the temperature at 41 degrees, and the stadium was packed with fans.

The Red Sox great started strong by getting the first three Yankees batters out. Meanwhile, the Red Sox’s offense was doing well. However, the Yankees’ Jorge Posada hit a solo home run in the second inning, giving the Yankees their first run. After that, Tim Wakefield didn’t allow any more Yankees to reach base in the second or third inning.

In the fourth inning, Derek Jeter got a single for the Yankees. However, when Álex Rodríguez came up to bat, he struck out swinging. Then, Jason Giambi walked, but Gary Sheffield hit into a double play, resulting in two outs for the Red Sox.

In the seventh inning, Tim Wakefield walked two Yankees with one out, which put the Red Sox in a tough spot. But he managed to get out of the inning without letting the Yankees score any runs. He had pitched for seven innings and got his first win of the 2004 season. He allowed four hits, all of them singles, and walked four batters. Doug Mirabelli, who usually caught for Tim Wakefield, had a good game and reached base four times, although one time was due to an error. The pitcher also prevented Alex Rodriguez from stealing a base. Keith Foulke closed the game with a scoreless ninth inning, and the Red Sox won the game with a final score of 6-2.

Oct. 16, 2004, The pitcher returns with a pride

Tim Wakefield was known for his selflessness both on and off the field. He was one of the most generous players in the league throughout his career and even after he retired. On the field, his selflessness was evident during the memorable 2004 ALCS against the Yankees. In Game 3, which was a blowout loss for the Red Sox, Tim Wakefield stepped in to help his team by pitching 3 ⅓ innings in a mop-up role. He also gave up his Game 4 start to contribute wherever the team needed him.

Tim Wakefield put his ego aside and played a crucial role in saving the Red Sox pitching staff during the 2004 ALCS. This was especially important because Games 4 and 5 of the series went into extra innings. His selflessness helped the team during their historic comeback from being down 3-0 in the series.

Then-Sox manager Terry Francona said that his biggest challenge had not been worrying about the final score of Game 3 but rather how they would be positioned for Game 4. Tim Wakefield mentioned that when Wakefield showed up in his spikes and volunteered to eat up innings in Game 3, sacrificing his Game 4 start, it immediately gave him renewed energy to work toward the next day.

Sept. 11, 2005, Tim Wakefield’s career-high performance

On September 11, 2005, Tim Wakefield had a remarkable game in the Bronx. His career will always be associated with the Yankees, both for good and bad reasons. However, in 2005, he delivered one of the best performances of his career at Yankee Stadium. Tim Wakefield struck out a career-high 12 batters and only allowed one run in a complete game during a crucial AL East showdown.

Even though Tim Wakefield played incredibly well, the Red Sox couldn’t secure a victory. Future Hall of Famers Randy Johnson and Mariano Rivera teamed up to shut out the Red Sox, and Tim Wakefield ended up with a loss in a 1-0 defeat.

Sept. 27, 2011: The last game against the Yankees

Tim Wakefield made his final appearance on the mound, but it wasn’t a fairy tale ending. In an attempt to prevent a historic September collapse, Wakefield gave up five runs in four innings against the rival Yankees. The Yankees won 6-2. The last batter he faced was Alex Rodriguez, who singled. During that play, Boston outfielder Carl Crawford made an error, resulting in an unearned run as Tim Wakefield’s career concluded.

Tim Wakefield vs. The Yankees

What do you think? Leave your comment below.