Chicago Cubs vs Pittsburgh Pirates Betting Pick & Prediction for 5/27

MLB game preview

The Chicago Cubs take on the Pittsburgh Pirates at PNC Park in an MLB regular season game. Both teams hold identical records of 29-26, but their recent performances differ. The Cubs are on a 10-game losing streak, while the Pirates have won their last three games.

Jameson Taillon will start for the Cubs, entering the game with a 2-4 record and a 5.20 ERA. The Pirates will counter with Bubba Chandler, who holds a 1-6 record and a 4.79 ERA. The game is set for Wednesday, May 27, 2026, at 6:40 PM, with the weather forecast predicting light rain. Fans can catch the game on SN LA.

Chicago Cubs Team Preview

The Chicago Cubs have struggled recently, dropping their last five games. Their most recent game against the Pittsburgh Pirates ended with a 12-1 loss. Jordan Wicks, the starting pitcher for that game, allowed eight earned runs in just over four innings.

Despite the losses, the Cubs have some strong hitters. Alex Bregman has maintained a batting average of .259, contributing significantly to the team’s offense. Michael Busch and Moisés Ballesteros both have six home runs, showing power at the plate.

On the mound, Jameson Taillon will start the next game for the Cubs. This season, he has a record of 2-4 with a 5.20 ERA. The Cubs will look to him to help break their losing streak against the Pirates.

Cubs vs Pirates Game Day Info

  • Sport: MLB
  • Teams: Chicago Cubs vs. Pittsburgh Pirates
  • Venue: PNC Park in Pittsburgh, PA
  • Date: Wednesday, May 27, 2026
  • Betting Odds: Cubs Moneyline -105, Pirates Moneyline -115, Cubs Runline -1.5 (+156), Pirates Runline +1.5 (-191), Total Over 8.5 (-121), Total Under 8.5 (+100)

Pittsburgh Pirates Team Preview

The Pittsburgh Pirates come into this game on a three-game winning streak. In their most recent game, they won 12-1 against the Chicago Cubs. Braxton Ashcraft was the starting pitcher, allowing just one earned run over 6 1/3 innings.

The Pirates’ hitting has been strong this season with a team batting average of .252, which ranks third in the league. Brandon Lowe has been a key player, leading the team with 13 home runs and a .270 batting average. The team also ranks in the top three for on-base percentage at .332.

Bubba Chandler will start on the mound for the Pirates. This season, he has a 4.79 ERA with 47 strikeouts. Chandler’s performance will be crucial for the Pirates as they look to continue their winning streak.

BTB Betting Pick

The Pirates are slightly favored with a moneyline of -115 against the Cubs at -105. The Pirates have a better batting average and pitching stats, which gives them an edge. Our pick is the Pirates to win the game with a projected score of 5-4.

The total for the game is set at 8.5. Both teams have solid offensive stats, with the Cubs ranking 2nd in on-base percentage. We recommend taking the over 8.5, expecting a total score of 9 runs.