The Cubs last played the Red Sox July 20, 2025 at Wrigley Field, 432 days ago. They lost 6-1 after winning the first two games of that series.
In hindsight, that’s when the wheels started falling off the 2025 season. The Cubs entered that game leading the NL Central by one game and were 20 games over .500 at 59-39. They went 33-30 after the July 20 loss, which isn’t terrible, but the Brewers went 38-25 and won the division by five games.
These games are more meaningful for the Cubs, as they could still
finish as the fourth, fifth or sixth NL postseason seed. Meanwhile, the Red Sox are most likely headed to New York Tuesday to begin a Wild Card series.
For more on the Red Sox, here’s Mike Carlucci, a writer for our SB Nation Red Sox site Over The Monster.
As the Cubs arrive in Fenway Park they face perhaps the most mercurial Red Sox team in a generation. Boston famously got off to a disastrous start. Alex Cora and the entire (well, mostly, Andrew Bailey survived) coaching staff departed unceremoniously, or perhaps slightly ceremoniously, in a van that said “Coaches for Hire.”
But then a 15-game winning streak. And a streak of 9. They couldn’t lose.
After about 40 gamers though, things slowed down. With a playoff berth clinched, Boston welcomes the Cubs to Fenway Park on a weekend the city braces for a nor-easter. Sunday became Friday afternoon. Friday evening became…slightly earlier on Friday. Saturday is… possibly being moved to Tropicana Field on Sunday. On the NESN post-game show the plan was for the players to be packed and ready to go to Tampa for a game Sunday and then from there to New York for the Wild Card.
Former Cub Willson Contreras hopes to play in the series after getting hit in the hand by the Texas Rangers. He’s still in a lot of pain trying to swing and isn’t sure he will be ready for the Wild Card. Garrett Crochet will probably not appear in any games. However they did move him to the Spring Training park to keep building up. Maybe if Sunday is played in Tampa he’ll make a surprise entrance?
Alex Gamboa will be the starter/opener in Game 1. He’s gone as deep as 4.0 innings before so it might be a short start rather than a strict open. It’s possible Jake Bennett provides some bulk innings as well. Bennett, in his rookie year, had a fantastic first half but tired in the second half.
Brayan Bello gets the start for Game 2. He’s been starting with an opener most of the summer but last time out against the Rays he went 8.0 brilliant innings in a return to starting the game in the first inning himself.
Who pitches on Saturday? It could be anyone! Possibly Jedixson Páez as he made one appearance for Boston already and could save the bullpen from carrying those innings. He’s tossed 6.2 innings in his career, all in 2026, with both colors of Sox while allowing 14 earned runs. You hate to think of a player as expendable but, in a potentially rain-shortened (or canceled) game 162 that is meaningless to at least one team involved, that just might be the bar.
Fun facts
This is only the second time that the Cubs have finished the regular season playing an American League team, and the first outside Chicago. They wrapped up 2020 on the South Side vs. the White Sox.
Since interleague play began in 1997, the Cubs have played only 27 games against the Red Sox, tying for their fewest against an American League team. They also have played 27 vs. the Athletics. They have played 28 vs. the Orioles and Rays, 29 vs. the Angels and 30, their total against Boston after this weekend, vs. the Blue Jays and Rangers.
The Cubs are 14-13 against the Red Sox, despite having been outscored by 11 runs, 142-131. The Cubs are +6 in all games except the second one in their last visit to Boston: a 17-0 shellacking on April 27, 2024.
The Cubs lost that series finale, too, 5-4, leaving each team with six wins when they have met in Boston. Half of the Cubs’ wins came in 2014, when they swept the Sox by scores of 2-0, 2-1 and 16-9. They went 1-2 in each of their three other series at Fenway Park. They split the first two games of all three.
(Courtesy BCB’s JohnW53)
Probable pitching matchups
Friday, Game 1: Clay Holmes, RHP (2-4, 4.26 ERA, 1.241 WHIP, 4.11 FIP in eight starts with Cubs; 6-8, 3.25 ERA, 1.165 WHIP, 3.62 FIP in 17 starts overall) vs. Alec Gamboa, LHP (1-0, 1.16 ERA, 1.065 WHIP, 3.16 FIP)
Friday, Game 2: David Peterson, LHP (6-2, 3.94 ERA, 1.394 WHIP, 4.20 FIP in 15 games with Cubs; 9-8, 4.96 ERA, 1.514 WHIP, 4.03 FIP in 31 games overall) vs. Brayan Bello, RHP (6-7, 4.62 ERA, 1.371 WHIP, 4.00 FIP)
Saturday: TBD vs. TBD
Times & TV channels
Friday, Game 1: 12:05 p.m. CT, Marquee Sports Network
Friday, Game 2: 5:05 p.m. CT, Marquee Sports Network
Saturday: 6:15 p.m. CT, Marquee Sports Network
As you have likely heard, there is a chance that the Saturday game might be moved to Tropicana Field in St. Petersburg, Florida, and played on Sunday instead of Saturday. If that happens, the game would likely be played at 2:05 p.m. CT so as to match up with all the other last day of the regular season starting times.
Prediction
I throw up my hands here. I have no idea. I like picking two of three so why the heck not. The Cubs need to win one more game than the Padres do this weekend against the Diamondbacks to finish ahead of them for a wild card spot, and one more game than the Phillies do against the Rays to finish ahead of them. (Those numbers include the fact that the Cubs own the tiebreaker against both the Padres and Phillies.)
Up next
The postseason! The Cubs will be playing Tuesday. Against … the Phillies, or the Padres, or the Braves, or even possibly the Diamondbacks, and at this time we have no idea where. As always, we await developments.
