Image Source: Bleed Cubbie Blue
Pirates vs Cubs headlines a critical National League series this weekend, with both teams entering the final stretch of the regular season and postseason pressure building. Chicago will host Pittsburgh for three games at Wrigley Field beginning Friday, September 11, with the Cubs trying to strengthen their wild-card position.
The Cubs currently trail the Philadelphia Phillies by one game for the top National League wild-card spot. Both teams have 15 games remaining, and Chicago owns the tiebreaker advantage. That margin makes every game increasingly important as the race for October baseball enters its decisive phase.
Pirates vs Cubs Series Carries Explosive October Stakes
Pittsburgh arrives in Chicago playing some of the best baseball in the majors. The Pirates recently swept the Chicago White Sox on the South Side, limiting them to only five runs across three games. Since August 24, Pittsburgh is 11-4, the best record in Major League Baseball during that span.
The Pirates have won four consecutive games and their last five series. They are also 8-2 over their past 10 games, putting them above .500 for the first time since July 29. Despite that surge, Pittsburgh remains 4.5 games behind the San Diego Padres for the final wild-card spot, leaving little room for error.
“Don’t look now, but the Pirates are getting hot at the right time,” Austin Bechtold of Bucs Dugout wrote. The team’s recent form has transformed what appeared to be a fading season into a fascinating late-September chase.
Shōta Imanaga Gives Chicago a Powerful Edge
Friday’s opener features a particularly favorable matchup for the Cubs. Shōta Imanaga will take the mound for Chicago against Pittsburgh opener Wilber Dotel. Imanaga has been nearly untouchable against the Pirates during his career, allowing only one run over 38 innings for a remarkable 0.24 ERA.
That history could be especially valuable with Pittsburgh forced into a likely bullpen game. The Pirates placed All-Star Braxton Ashcraft on the 15-day injured list Thursday because of right arm discomfort. Dotel is expected to begin Friday’s contest, while Khristian Curtis and recently recalled Antwone Kelly could handle bulk innings.
- Friday: Shōta Imanaga vs. Wilber Dotel, 1:20 p.m. CT
- Saturday: Clay Holmes vs. Paul Skenes, 1:20 p.m. CT
- Sunday: Matthew Boyd vs. Bubba Chandler, 1:20 p.m. CT
All three games will be carried by Marquee Sports Network. Friday’s matchup will also air on MLB Network outside the Cubs and Pirates’ home market territories.
Paul Skenes Sets Up a Marquee Saturday Showdown
Saturday could provide the weekend’s most compelling pitching battle. Paul Skenes will start for Pittsburgh against former Pirate Clay Holmes, who joined the Cubs from the New York Mets at the trade deadline. Holmes has posted a 3.51 ERA through his first six starts with Chicago and owns a 2.83 ERA in 15 starts overall this season.
Skenes enters with a 10-11 record, 3.83 ERA, 1.148 WHIP and 3.09 FIP. Although the rookie has been one of baseball’s most electric arms, Chicago has experienced success against him in the past. Matthew Boyd is scheduled to face Bubba Chandler in Sunday’s finale.
Oneil Cruz Powers Pittsburgh’s Late Surge
Oneil Cruz has been a major catalyst for the Pirates since returning August 18 after missing nearly two months with a hand injury. He is batting .315 with four home runs and 18 runs batted in during that stretch. On Thursday, Cruz hit a 117.4-mph solo home run, the hardest-hit homer of his season, while driving in both Pittsburgh runs.
Konnor Griffin has also returned, and first baseman and right fielder Ryan O’Hearn could rejoin the team this weekend. Those reinforcements give Pittsburgh additional offensive depth at exactly the moment its postseason hopes are being tested.
The Cubs, however, cannot afford to focus only on Pittsburgh’s momentum. Chicago is 6-10 since August 24 and needs to reverse that trend quickly. Historically, the Cubs have dominated this matchup at Wrigley Field, going 31-10 against the Pirates from June 2018 through June 2023. Since then, though, Chicago is only 9-11 at home and has never won the first two games of a series against Pittsburgh.
Bleed Cubbie Blue predicts the Cubs should win at least two of three, particularly with Ashcraft unavailable and Imanaga scheduled for Friday. A strong series could stabilize Chicago’s wild-card position, while another difficult weekend would make the final 15 games considerably more stressful.
FAQ: Pirates vs Cubs Series
When does the Pirates vs Cubs series begin?
The series begins Friday, September 11, 2026, at 1:20 p.m. Central Time at Wrigley Field in Chicago.
Who is pitching Friday?
Shōta Imanaga is scheduled to start for the Cubs, while Wilber Dotel is expected to open for the Pirates in a likely bullpen game.
Who starts Saturday’s game?
Clay Holmes is scheduled to pitch for Chicago against Pittsburgh ace Paul Skenes.
Why is this series important?
Chicago is chasing a top wild-card position, while Pittsburgh is trying to overcome a 4.5-game deficit in the race for the National League’s final postseason spot.
What comes next for the Cubs?
Chicago will host the Atlanta Braves in a three-game series at Wrigley Field beginning Monday evening.
