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Pirates vs Cubs Prediction 5/28/26 MLB Picks Today

Chicago Cubs (30-26) vs. Pittsburgh Pirates (29-27)
May 28, 2026 6:40 pm EDT
The Line: Pittsburgh Pirates -175 / Chicago Cubs 144; Over/Under: 7.5
(Get latest betting odds)

The Chicago Cubs and Pittsburgh Pirates meet Thursday in MLB action at PNC Park. Here’s a Pirates vs Cubs Prediction. This article will include a Pirates vs Cubs Pick.

Chicago Cubs Betting Preview

The Chicago Cubs are 30-26 on the year and play the Athletics and Cardinals next. The Chicago Cubs are batting .238 on the season and have a .336 OBP and a .389 slugging percentage. The Chicago Cubs’ pitching staff has a 4.22 ERA and a 1.24 WHIP. Alex Bregman leads the Chicago Cubs with 58 hits and 16 RBI, while Michael Busch and Nico Hoerner have combined for 102 hits and 63 RBI.


Colin Rea gets the ball for the Chicago Cubs, and he is 4-3 with a 4.83 ERA and 44 strikeouts this season. Rea is 3-3 with a 5.09 ERA and 32 strikeouts in his career against the Pittsburgh Pirates.

Pittsburgh Pirates Betting Preview

The Pittsburgh Pirates are 29-27 on the year and play the Twins and Astros next. The Pittsburgh Pirates are batting .252 on the season and have a .332 OBP and a .392 slugging percentage. The Pittsburgh Pirates’ pitching staff has a 3.81 ERA and a 1.24 WHIP. Oneil Cruz leads the Pittsburgh Pirates with 58 hits and 35 RBIs, while Nick Gonzales and Bryan Reynolds have combined for 108 hits and 56 RBIs.

Paul Skenes gets the ball for the Pittsburgh Pirates, and he is 6-4 with a 3.00 ERA and 65 strikeouts this season. Skenes is 2-2 with a 2.94 ERA and 43 strikeouts in his career against the Chicago Cubs.

Why the Pittsburgh Pirates will win

  • The Cubs have lost 10 of their last 11 games.
  • The Pirates have won five of their last six home games against NL Central opponents.
  • The Cubs have failed to cover the run line in 10 of their last 11 games.
  • The Pirates have covered the run line in each of their last six Thursday night games against NL Central opponents that held a winning record.
  • The Cubs have trailed after 3 innings in five of their last six games against opponents that held a winning record.
  • The Cubs have trailed after 5 innings in seven of their last eight games as road underdogs against NL Central opponents.
  • The Cubs have lost the first inning in three of their last four games as underdogs.

Why the Chicago Cubs will win

  • The Cubs have won nine of their last 10 games as road underdogs against the Pirates.
  • The Pirates have lost each of their last five games as favorites against the Cubs following a loss.
  • The Cubs have covered the run line in each of their last eight Thursday road games against National League opponents.
  • The Pirates have failed to cover the run line in 10 of their last 11 home games against NL Central opponents following a loss.
  • The Cubs have led after 5 innings in nine of their last 12 night games against the Pirates.

Total Runs Facts

  • Eight of the Pirates’ last nine games as favorites against NL Central opponents have gone OVER the total runs line.
  • Five of the Cubs’ last six road games have gone OVER the total runs line.
  • The ‘Inning 1 OVER 0.5 runs’ market has hit in each of the Cubs’ last seven games as underdogs against NL Central opponents.
  • The ‘Inning 1 OVER 0.5 runs’ market has hit in each of the Pirates’ last four games as favorites.

Pittsburgh Pirates Player Prop Facts

  • Bryan Reynolds has hit a home run in five of the Pirates’ last nine games as home favorites against the Cubs.
  • Marcell Ozuna has recorded at least one hit in each of his last eight appearances with his team as a favorite against the Cubs.
  • Oneil Cruz is one of only two players to record 10+ Home Runs and 10+ Stolen Bases this season.

Chicago Cubs Player Prop Facts

  • Alex Bregman has recorded at least one hit in each of his last 13 road appearances.
  • Michael Conforto has hit a home run in two of his last three road appearances.

Matchup/League Facts

  • The Pirates rank T2nd in the league for hits this season (482).
  • The Pirates rank 29th in the league for strikeouts against this season (511).
  • The Cubs rank 1st in the league for walks this season (248).
  • The Cubs rank 29th in the league for home runs allowed this season (76).

Pirates vs Cubs Prediction

The Cubs have been a mess over the last two weeks, and a win yesterday doesn’t make us forget. Skenes hasn’t been as lights out as he’s capable of being, but that stretch is coming sooner or later. He’s one of the best arms in the sport. In 34.1 home innings, Skenes has a 2.62 ERA and a .172 allowed batting average. I doubt the struggling Cubs are going to be thrilled to see Skenes on the bump. I’m going to side with the Pirates and the RL for max betting value.

Randy Chambers's Free Pick: Pittsburgh Pirates -1.5

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Randy Chambers

Randy has covered sports betting since 2014 and writes about everything from NFL to WNBA. Follow Randy Chambers on Twitter.

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