Top Five Red Sox Performances Against Cubs At Wrigley Field

The Boston Red Sox and the Chicago Cubs represent two of baseball’s most historic franchises and play at two of the game’s premier venues in Fenway Park and Wrigley Field, respectively.

For as much history as each team holds, this weekend marks just the fourth series the Red Sox have played at Wrigley Field. Boston first visited Wrigley Field in 2005, one year after winning its first World Series in 86 years while the Cubs played through the 97th season of the “Billy Goat” curse. Chicago did break its own curse with a championship in 2016. 

With only nine games between the teams at Wrigley Field, the Red Sox have seen some memorable individual performances during these meetings. 

Here is a look back at five of the best Red Sox performances in Chicago:

1. Tim Wakefield — June 12, 2005 
On Sunday Night Baseball, Tim Wakefield delivered a gem as the Red Sox salvaged the series finale in an 8-1 win. The knuckleballer tossed seven innings of one-run ball, allowing just four hits and striking out three Cubs. Wakefield also scored a run in the sixth inning after reaching on a fielder’s choice.

2. David Ortiz — June 10, 2005
In the first-ever Red Sox-Cubs matchup at Wrigley, David Ortiz made sure to leave his mark and showcase his trademark power. The Sox slugger hit two home runs to drive Boston’s offense despite a 14-6 loss. Ortiz hit a solo shot off of Greg Maddux in the sixth inning. In the ninth, Ortiz demolished a hanging breaking ball for a two-run home run that landed in the trees outside of the stadium in right field.

3. Jarren Duran — July 1-3, 2022
As the Red Sox returned to the North Side of Chicago for the first time in 10 years, Jarren Duran took his chance to make an impact throughout the weekend. Duran hit .357 in the series, including a leadoff home run on the first pitch of the series to straight away center field. The speedy outfielder also drew a bases-loaded walk to put Boston in front in the fourth inning of the team’s lone win of the series in the finale of the three-game set. 

Amid a breakout 2023 season (.320 AVG, .886 OPS, tied for third in Major League Baseball with 27 doubles), Duran looks to produce at Wrigley for the second straight season.

4. Johnny Damon — June 12, 2005
As Wakefield kept the Cubs lineup at bay, Johnny Damon drove Boston’s offense in a primetime 8-1 win as the bats homered four times. Damon went 3-for-5 with a two-run triple, a solo home run and three runs batted in. The outfielder reached base four times as he added a walk and tallied nine total bases.

5. Jon Lester — June 16, 2012
Jon Lester took the ball for Boston in the first of back-to-back wins in Chicago to deliver the franchise’s lone series win at Wrigley. The left-hander earned the victory after dealing 6 2/3 innings. He allowed three earned runs and struck out eight batters. Lester began the outing with six scoreless innings before Bobby Valentine called to the bullpen with two outs in the seventh inning. The Red Sox evened the series with a 4-3 win.