Chicago Cubs vs Pittsburgh Pirates Prediction, Preview and Odds - 05/28/2026

Game Time: 6:40 pm ET, Thursday, May 28, 2026

Venue:  PNC Park, Pittsburgh, PA 

Where to Watch:  MLB TV

DraftKings:  Moneyline odds:  Cubs +144, Pirates -175; Over/Under:  7.5 runs

Bet365:  Moneyline odds:  Cubs +145, Pirates -175; Over/Under:  7.5 runs

BetMGM:  Moneyline odds:  Cubs +145, Pirates -175; Over/Under:  7.5 runs

Chicago Cubs:  29-26 (5th place, NL Central)

Pittsburgh Pirates:  29-26 (4th place, NL Central)

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Chicago Cubs:  0-10 last 10

Pittsburgh Pirates:  5-5 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 29-26 record overall and have a road record of 11-15. This is the series finale of a 4-game series with the Pirates on Thursday with the 3rd game of this series still to be played on Wednesday. The Cubs lost the series opener on Monday and the 2nd game on Tuesday. Their offense ranks 10th in the MLB with a .718 OPS. Jameson Taillon is their starting pitcher on Wednesday while Colin Rea is making his start in this game on Thursday. He is 4-3 with a 4.83 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 3 ER, 2 HR, and 3 BB with 4 SO on 4 hits through 7 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 29-26 record overall and have a home record of 15-13. This is the 4th game of a 4-game series with the Cubs on Thursday with the 3rd game of this series still to be played on Wednesday. The Pirates won the 1st game of this series on Monday and the 2nd game on Tuesday. Their offense ranks 6th in the MLB with a .724 OPS. Bubba Chandler is their starting pitcher on Wednesday while Paul Skenes is making his start in this game on Thursday. He is 6-4 with a 3.00 ERA this season. His team lost their last 2 straight games this season with him making an appearance. In his last MLB regular season start, he allowed 4 earned runs, 1 homer, and 1 walk with 2 strikeouts on 9 hits through 5 innings pitched against the Toronto Blue Jays.

The current betting odds have the Pirates listed as a favorite in this game according to Draftkings Sportsbook. The Pirates have looked good in their games this season with their 29-26 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 15-13 home record this season. Meanwhile, the Cubs have looked good in their games this season with their 29-26 record overall which has them right in the middle of the NL Central. They haven't been a good road team though with their 11-15 road record this year. The Cubs have looked a lot worse in their road games this year and lately they have been terrible, going 0-10 in their last 10 games. They have had a good offense this season, but they have been in a big slump lately and even their offense has been bad. The Pirates haven't looked that great lately, going 5-5 in their last 10 games, but they have looked better in their last few games and they are going to have the edge in this one. They have had a good offense this season too, looking good in their games lately, and they are going to have the better pitching matchup. Skenes is on the mound for the Pirates in this one and he has looked great this season since having that bad start to start the year. He is 6-4 with a 3.00 ERA and he has looked great since coming into the league. He did give up 4 earned runs in his last start and the team has lost 2 games in a row now with him starting, but that hasn't been a common theme for him and they can take advantage of the Cubs in this terrible slump. The Cubs are going with Rea in this one and he hasn't looked great this year. He is 4-3 with a 4.83 ERA and he has been giving up quite a few runs this season. He gave up 3 earned runs in his last start which has been a common theme for him and the team has lost 3 games in a row now with him starting. It is tough to see the Cubs breaking out of this slump with their pitching issues at the moment and their offense not performing, so look for the Pirates to keep rolling in this one. The best way to place a bet here is on the Pirates to win this game. 

Cubs Pirates Prediction:  Our MLB Pick for Thursday, May 28, 2026 (6:40 pm ET start time) is Pirates 5 Cubs 3.

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Chicago Cubs: 209-178 (+9.5 units) on the moneyline in all games. 169-129 (+25.8 units) on the moneyline against right-handed starters. 13-8 (+13.7 units) on the moneyline as an underdog of +150 or more. 11-4 OVER as a road underdog of +100 or higher.

Pittsburgh Pirates: 177-202 (-15.4 units) on the moneyline in all games. 73-57 (-6.3 units) on the moneyline as a favorite of -110 or higher. 58-68 (-8.3 units) on the moneyline against division opponents. 14-7 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.

“It doesn’t matter what they’re doing. You don’t deliver every time, but we gotta have some level of production. Pressing? I don’t know. I’m not sure what the answer is to that. The answer is it’s a big-league at-bat with men on base. It’s the at-bat you want in a game. It’s the at-bat you can make a difference for your team. It’s the at-bat you can flip the course of a game. And it’s time for us to deliver.” - Craig Counsell after his team’s 10th straight loss in their game against the Pirates on Tuesday. 

"He’s shown a lot. To come up in a bulk role in the ‘pen, close a game against the Phillies, start games, back to the bullpen, back to starting, and then to come into the year this year fighting for a spot in the rotation in the spring, then to earn one and run with it the way that he has, he continues to get better. The stuff has gotten better and the execution – pitching in the strike zone, getting the swing and miss, getting ahead. He’s really, even today, was extremely efficient.” - Don Kelly on Braxton Ashcraft after his team’s win against the Cubs in their game on Tuesday. 

Pete Crow-Armstrong (L) CF

Nico Hoerner (R) 2B

Michael Busch (L) 1B

Alex Bregman (R) 3B

Ian Happ (S) LF

Seiya Suzuki (R) RF

Moisés Ballesteros (L) DH

Carson Kelly (R) C

Dansby Swanson (R) SS

Konnor Griffin (R) SS

Brandon Lowe (L) 2B

Bryan Reynolds (S) LF

Nick Gonzales (R) 3B

Oneil Cruz (L) CF

Marcell Ozuna (R) DH

Esmerlyn Valdez (R) RF

Spencer Horwitz (L) 1B

Henry Davis (R) C

Batting Average:  Carson Kelly (.300)

Hits:  Alex Bregman (56)

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 (58)

Home Runs:  Brandon Lowe (13)

RBI:  Oneil Cruz (35)

Stolen Bases:  Oneil Cruz (17)

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)