Cubs vs Pirates Prediction 5/27/26 MLB Picks Today

In this article, we will formulate a Cubs vs Pirates Prediction for this MLB matchup on Wednesday, May 27^th in the third game of this series. Let’s take a look at the prediction for this MLB matchup.

Pittsburgh Pirates Preview

The Pittsburgh Pirates have a 29-26 record this season and are sitting in the fourth place of the NL Central. They have a 15-13 home record and are coming off a 12-1 home win against the Cubs. They will face the Twins and the Astros next.

The Pirates have a .252 batting average this season, .333 OBP and .391 Slugging percentage. Pittsburgh’s pitching staff has a 3.74 ERA and 1.23 WHIP. Nick Gonzales is the team’s best hitter with a .304 batting average. Oneil Cruz leads the team in RBI with 35, while Brandon Lowe adds a team-high 13 home runs.

Bubba Chandler (R) is the projected starting pitcher for the Pirates, and he has a 1-6 record, 4.79 ERA and 1.47 WHIP.

Chicago Cubs Preview

The Chicago Cubs have a 29-26 record this season and are sitting in the fifth place of the NL Central. They have a 11-15 away record and are coming off a 1-12 road defeat against the Pirates. They will face the Cardinals and the Athletics next.

The Cubs have a .236 batting average this season, .333 OBP and .385 Slugging percentage. Chicago’s pitching staff has a 4.23 ERA and 1.24 WHIP. Alex Bregman is the team’s best hitter with a .259 batting average. Nico Hoerner leads the team in RBI with 31, while Ian Happ adds a team-high 10 home runs.

Jameson Taillon (R) is the projected starting pitcher for the Cubs, and he has a 2-4 record, 5.20 ERA and 1.27 WHIP.

The Chicago Cubs @ Pittsburgh Pirates Betting Trends: May 27, 2026

• Probable Starting Pitcher: Bubba Chandler      Record this season: 1-6      ERA: 4.60
• Home Record: 1-3
• Last 5 against Cubs: 0-0

Why the Pittsburgh Pirates will win

• The Cubs have lost each of their last 10 games.
• The Pirates have won seven of their last eight games against NL Central opponents.
• The Cubs have failed to cover the run line in each of their last 10 games.
• The Pirates have covered the run line in each of their last five games against the Cubs.
• The Pirates have won the first inning in four of their last five games as favorites against NL Central opponents.
• The Cubs have trailed after 3 innings in seven of their last eight games.
• The Cubs have trailed after 5 innings in each of their last seven games as road underdogs against NL Central opponents.

• Probable Starting Pitcher: Jameson Taillon      Record this season: 2-4      ERA: 5.20
• Road Record: 1-3
• Last 5 against Pirates: 3-0

Why the Chicago Cubs will win

• The Cubs have won each of their last nine Wednesday games as underdogs against NL Central opponents.
• The Pirates have lost nine of their last 10 games against the Cubs following a home win.
• The Cubs have covered the run line in each of their last 12 Wednesday games as underdogs against NL Central opponents.
• The Pirates have failed to cover the run line in each of their last nine Wednesday night games as favorites against NL Central opponents.
• The Cubs have led after 5 innings in six of their last seven night games against the Pirates.
• The Cubs have led after 3 innings in seven of their last eight Wednesday games against NL Central opponents that held a winning record.

Total Runs Facts

• Seven of the Pirates’ last eight games as favorites against NL Central opponents have gone OVER the total runs line.
• Eight of the Cubs’ last 10 games as underdogs against the Pirates have gone OVER the total runs line.
• The ‘Inning 1 OVER 0.5 runs’ market has hit in each of the Cubs’ last six games as underdogs against NL Central opponents.
• The ‘Inning 1 OVER 0.5 runs’ market has hit in each of Bubba Chandler’s last four appearances as a starter.

Pittsburgh Pirates Player Prop Facts

• Bryan Reynolds has hit a home run in five of the Pirates’ last eight games as home favorites against the Cubs.
• Marcell Ozuna has recorded at least one hit in each of his last seven 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

• Seiya Suzuki has hit a home run in two of the Cubs’ last three games as road underdogs against NL Central opponents.
• Jameson Taillon has recorded a win in each of his last three road appearances against former teams.
• Jameson Taillon has recorded five or more strikeouts in eight of his last nine appearances at PNC Park against opponents that held a winning record.
• Alex Bregman has recorded at least one hit in each of his last 12 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).

Cubs vs Pirates Prediction

The Pirates are 4-1 in their last 5 meetings against the Cubs and have won their last two meetings in Pitssburgh.

In this Cubs vs Pirates Prediction, the Pirates are coming as -115 home favorites. The Cubs’ downfall continues, as they are now 2-14 in their last 16 games and are putting Jameson Taillon on the mound, who has 12 earned runs in his last two starts. He also got torched in his previous start against the Pirates this season, giving up 6 runs and has been terrible on the road with a 6.04 road ERA. Chicago is dead last against righties in the past couple of weeks, so keep fading them until further notice. Take the Pirates in this one.