Cubs vs Pirates Prediction 5/27/2026 Today’s MLB Picks

In this article we will formulate a Cubs vs Pirates prediction for this MLB game on Wednesday, May 27th at PNC Park in Pittsburgh, Pennsylvania. Let’s take a look at the prediction for this MLB matchup. 

Chicago Cubs Betting Preview

The Chicago Cubs are 29-26 this year after they lost the first two games in this series by scores of 1-2 and 1-12. In game two, Chicago cut the deficit to 5-1 in the second inning, but couldn’t find anymore offense in the ugly loss. The Cubs recorded eight hits and they committed one error, while they were led by Happ, who went 1-4 with one RBI in the game. Wicks allowed nine hits and eight earned runs over 4.1 innings for the loss, while Milner allowed two earned runs in relief. Prior to this series, Chicago lost all three against the Astros and all three against the Brewers.

This season, Chicago has a 4.23 ERA with a 1.24 WHIP and a .240 opponent batting average, while they have scored 255 runs with a .236 batting average and a .333 on base percentage. Nico Hoerner has led the Cubs with four home runs and 31 RBIs, while Dansby Swanson has added seven home runs and 27 RBIs. The projected starting pitcher for Chicago is Jameson Taillon, who is 2-4 with a 5.20 ERA and a 1.27 WHIP over 55.1 innings pitched this year. 

Pittsburgh Pirates Betting Preview

The Pittsburgh Pirates are 29-26 this season after they won game two by a score of 12-1 last night. Pittsburgh scored five runs in the first inning and they blew the game open for the lopsided win. The Pirates recorded 15 hits and they committed three errors in the game, while they were led by Valdez, who went 1-4 with one home run and three RBIs. Ashcraft allowed seven hits and one earned run over 6.1 innings for the win, while Santana closed out the game. Prior to this series, Pittsburgh lost two out of three against the Blue Jays, but did win two out of three against the Cardinals before that. 

This season, Pittsburgh has a 3.72 ERA with a 1.23 WHIP and a .225 opponent batting average, while they have scored 270 runs with a .252 batting average and a .333 on base percentage. Oneil Cruz has led the Pirates with 11 home runs and 35 RBIs, while Brandon Lowe has added 13 home runs and 33 RBIs. The projected starting pitcher for Pittsburgh is Bubba Chandler, who is 1-6 with a 4.79 ERA and a 1.47 WHIP over 47.0 innings pitched this season. 

Why the Pittsburgh Pirates will win

• The Cubs have lost each of their last nine road games against NL Central opponents.
• The Pirates have won each of their last five home games against NL Central opponents.
• The Cubs have failed to cover the run line in each of their last nine games after playing the previous day.
• The Pirates have covered the run line each of their last four games against teams that held a winning record.
• The Pirates have led after 3 innings in each of their last four games against the Cubs.
• The Pirates have won the first inning in three of their last four games as home favorites against NL Central opponents.
• The Pirates have led after 5 innings in each of their last four night games against NL Central opponents.

Why the Chicago Cubs will win

• The Cubs have won eight of their last nine games as road underdogs against the Pirates.
• The Pirates have lost three of their last four games as home favorites against the Cubs following a win.
• The Pirates have failed to cover the run line in each of their last nine Wednesday night games as home favorites against NL Central opponents.
• The Cubs have covered the run line in each of their last seven Wednesday games as road underdogs against NL Central opponents.

Total Runs Facts

• Five of the Pirates’ last six games as favorites against National League opponents have gone OVER the total runs line.
• Four of the Cubs’ last five road games have gone OVER the total runs line.
• The ‘Inning 1 UNDER 0.5 runs’ market has hit in seven of Jameson Taillon’s last eight road appearances as a starter.
• The ‘Inning 1 OVER 0.5 runs’ market has hit in five of the Pirates’ last six games.

Pittsburgh Pirates Player Prop Facts

• Bryan Reynolds has hit a home run in five of the Pirates’ last 10 games as favorites against the Cubs.
• Oneil Cruz has recorded at least one hit in each of the Pirates’ last seven games as home favorites against the Cubs.

Chicago Cubs Player Prop Facts

• Dansby Swanson has hit a home run in three of his last seven appearances with his team as a road underdog against the Pirates.
• Jameson Taillon has recorded five or more strikeouts in seven of his last eight appearances at PNC Park against NL opponents that held a winning record.
• Alex Bregman has recorded at least one hit in each of his last 11 road appearances after playing the previous day.
• Jameson Taillon has recorded a win in three of his last four appearances against former teams.

Cubs vs Pirates Prediction 

Chicago comes into this matchup desperately trying to snap their losing streak, but they have scored one run or fewer in three of their last four games. The Cubs are 11-15 on the road this year, while the Pirates are 15-13 at home. Pittsburgh has won three in a row and they have allowed one run in each of those three wins. The Pirates are starting Chandler, who has allowed two earned runs or fewer in three of his last four starts, while Taillon has allowed 12 earned runs over his last 9.2 innings. Take the Pirates to get another win at home here.

David Racey's Pick: Pirates ML