Chicago Cubs vs Pittsburgh Pirates Prediction, Preview and Odds - 05/27/2026

Game Time: 6:40 pm ET, Wednesday, May 27, 2026

Venue:  PNC Park, Pittsburgh, PA 

Where to Watch:  MLB TV

DraftKings:  Moneyline odds:  Cubs -105, Pirates -115; Over/Under:  8.5 runs

Bet365:  Moneyline odds:  Cubs -105, Pirates -115; Over/Under:  8.5 runs

BetMGM:  Moneyline odds:  Cubs -105, Pirates -115; Over/Under:  8.5 runs

Chicago Cubs:  29-25 (3rd place, NL Central)

Pittsburgh Pirates:  28-26 (5th place, NL Central)

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Chicago Cubs:  1-9 last 10

Pittsburgh Pirates:  4-6 last 10

The Cubs are entering this series off a loss and got swept in their 3-game series against the Houston Astros 3-0 in their last series. They enter this game with a 29-25 record overall and have a road record of 11-14. This is the 3rd game of a 4-game series with the Pirates on Wednesday with the 2nd game of this series still to be played on Tuesday. The Cubs lost the series opener on Monday. Their offense ranks 8th in the MLB with a .721 OPS. Jordan Wicks is their starting pitcher on Tuesday while Jameson Taillon is making his start in this game on Wednesday. He is 2-4 with a 5.20 ERA this season. His team lost their last 3 straight games this season with him making an appearance. In his last MLB regular season appearance, he allowed 4 ER, 1 HR, and 1 BB with 5 SO on 8 hits through 4.2 IP against the Houston Astros.

The Pirates are entering this series off a win and lost their 3-game series against the Toronto Blue Jays 2-1 in their last series. They enter this game with a 28-26 record overall and have a home record of 14-13. This is the 3rd game of a 4-game series with the Cubs on Wednesday with the 2nd game of this series still to be played on Tuesday. The Pirates won the 1st game of this series on Monday. Their offense ranks 11th in the MLB with a .717 OPS. Braxton Ashcraft is their starting pitcher on Tuesday while Bubba Chandler is making his start in this game on Wednesday. He is 1-6 with a 4.79 ERA this season. His team lost their last 6 straight games this season with him making an appearance. In his last MLB regular season start, he allowed 1 earned run, 0 homers, and 3 walks with 11 strikeouts on 2 hits through 5 innings pitched against the Toronto Blue Jays.

The current betting odds have the Cubs listed as a slight underdog in this game according to Draftkings Sportsbook. The Pirates have looked good in their games this season with their 28-26 record overall which has them right at the bottom of the NL Central. They haven't looked great in their own ballpark though with their 14-13 home record this season. Meanwhile, the Cubs have looked good in their games this season with their 29-25 record overall which has them right in the middle of the NL Central. They haven't been a good road team though with their 11-14 road record this year. The Cubs have looked a lot worse on the road this year and lately they have looked terrible, going 1-9 in their last 10 games as they have been in a huge slump, but the Pirates are 4-6 in their last 10 and have had some trouble themselves. The Cubs are going with Taillon in this one and he hasn't looked great this season. He is 2-4 with a 5.20 ERA and the team hasn't had a lot of success with him lately. They have lost 3 games in a row now with him starting and he also gave up 4 earned runs in his last start which has been a common theme for him, but he hasn't been this bad over the last few seasons and he will be looking to turn things around. The Pirates are going with Chandler in this one and he hasn't looked any better this season. He is 1-6 with a 4.79 ERA and his team hasn't had a ton of success with him either. He is off a good start in which he only gave up 1 earned run, but that hasn't been a common theme for him this year and the team has still lost 6 games in a row now with him starting. The Cubs have been in an offensive slump too, but they do have a really good offense that is going to start hitting again and this could be the game they need to break out of their slump. Look for the Cubs to take advantage of this young starter and break this terrible losing streak they have been on. The best way to place a bet here is on the Cubs to win this game. 

Cubs Pirates Prediction:  Our MLB Pick for Wednesday, May 27, 2026 (6:40 pm ET start time) is Cubs 4 Pirates 2.

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Chicago Cubs: 209-177 (+10.5 units) on the moneyline in all games. 169-128 (+26.8 units) on the moneyline against right-handed starters. 31-21 (+5.6 units) on the moneyline vs. a starting pitcher whose lasts less than 5 innings per start. 10-4 OVER as a road underdog of +100 or higher.

Pittsburgh Pirates: 176-202 (-16.4 units) on the moneyline in all games. 72-57 (-7.3 units) on the moneyline as a favorite of -110 or higher. 57-68 (-9.3 units) on the moneyline against division opponents. 13-7 OVER when playing against a team with a winning record.

Chicago Cubs:  E. Cabrera (SP) Fifteen Day IL - Finger. M. Shaw (RF) Ten Day IL - Back. M. Boyd (SP) Fifteen Day IL - Knee. R. Martin (RP) Fifteen Day IL - Elbow. P. Hodge (RP) Sixty Day IL - Elbow. C. Horton (SP) Sixty Day IL - Forearm. H. Harvey (RP) Sixty Day IL - Tricep. J. Steele (SP) Sixty Day IL - Elbow. T. Austin (1B) Sixty Day IL - Knee. S. Miller (RP) Sixty Day IL - Elbow.

Pittsburgh Pirates:  R. O'Hearn (RF) Ten Day IL - Quad. J. Bart (C) Ten Day IL - Foot Infection. C. Devenski (RP) Fifteen Day IL - Illness. J. Jones (SP) Sixty Day IL - Elbow.

“I mean, he’s, it’s it’s, Ian goes through phases of hot and cold like every other hitter does. Um, you know, I think he’s just, but his strength is the ball-strike recognition and then being able to handle that part of it.” - Craig Counsell on Ian Happ after his team’s loss against the Pirates in their game on Monday. 

“Three innings out of the bullpen in that situation, and such a close game, mixed speeds, threw strikes. He was tremendous.” - Don Kelly on Wilber Dotel after his team’s win against the Cubs in their game on Monday.

Pete Crow-Armstrong (L) CF

Ian Happ (S) LF

Michael Busch (L) 1B

Alex Bregman (R) 3B

Michael Conforto (L) RF

Pedro Ramírez (S) 2B

Moisés Ballesteros (L) DH

Miguel Amaya (R) C

Dansby Swanson (R) SS

Spencer Horwitz (L) 1B

Brandon Lowe (L) 2B

Bryan Reynolds (S) RF

Nick Gonzales (R) 3B

Oneil Cruz (L) CF

Marcell Ozuna (R) DH

Konnor Griffin (R) SS

Jhostynxon Garcia (R) LF

Henry Davis (R) C

Batting Average:  Carson Kelly (.294)

Hits:  Alex Bregman (54)

Home Runs:  Ian Happ (10)

RBI:  Nico Hoerner (31)

Stolen Bases:  Pete Crow-Armstrong (12)

Wins:  Shota Imanaga (4)

Saves:  Daniel Palencia (3)

ERA:  Ty Blach (0.00)

Batting Average:  Endy Rodríguez (.316)

Hits:  Oneil Cruz (55)

Home Runs:  Brandon Lowe (13)

RBI:  Oneil Cruz (34)

Stolen Bases:  Oneil Cruz (16)

Wins:  Paul Skenes (6)

Saves:  Gregory Soto (6)

ERA:  Evan Sisk (1.61)

Managers:

Chicago Cubs: Craig Counsell (3rd season)

Pittsburgh Pirates: Don Kelly (2nd season)