Chicago Cubs vs Pittsburgh Pirates Picks and Prediction for Wednesday May 27 2026
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The Chicago Cubs travel to face the Pittsburgh Pirates on Wednesday, May 27, 2026, at PNC Park in Pittsburgh, Pennsylvania. First pitch is scheduled for 6:40 PM ET with coverage available on MLB.TV. The game-time weather is expected to be 73 degrees. At the time of this writing the odds were not released. Be sure to check out our free MLB picks.
Starting Pitchers Look to Reverse Recent Trends
The Cubs are expected to start Jameson Taillon, who enters with a 2-4 record, a 5.20 ERA, a 1.27 WHIP, 55.1 innings pitched, 52 hits allowed, 47 strikeouts, 18 walks, and 17 home runs allowed. Pittsburgh is projected to counter with Bubba Chandler, who comes into the matchup with a 1-6 record, a 4.79 ERA, a 1.47 WHIP, 47.0 innings pitched, 35 hits allowed, 47 strikeouts, 34 walks, and seven home runs allowed. Both starters have faced difficulties this season, though Pittsburgh’s projected starter enters with the lower ERA while Chicago’s starter has allowed significantly more home runs.
Chicago Trying to Snap Extended Losing Streak
Chicago enters this matchup with a 29-25 overall record and an 11-14 road record. The Cubs recently lost to Pittsburgh by a 2-1 score and have now dropped five straight games overall. Chicago also recently lost to Houston in three consecutive contests before that setback. During the current losing streak, the Cubs have struggled offensively, scoring two runs or fewer in four of the five losses.
The Cubs are batting .237 as a team with 254 runs, 430 hits, 61 home runs, a .334 on-base percentage, and a .387 slugging percentage. On the mound, Chicago owns a 4.09 ERA, a 1.23 WHIP, 164 walks, 434 strikeouts, and a .236 opponent batting average. The Cubs have shown strong power production with 61 home runs and continue to hold one of the stronger run totals among the teams provided.
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One of the major concerns for Chicago entering this game is offensive consistency during the recent losing streak. Despite solid season-long numbers in runs and home runs, the Cubs have struggled to finish scoring opportunities lately. The pitching staff has remained respectable overall, but the lack of run support has become a major issue over the last several games.
Pittsburgh Looking to Continue Recent Momentum
Pittsburgh enters Wednesday’s game with a 28-26 overall record and a 14-13 home record. The Pirates recently won over Chicago by a 2-1 score after also recently winning over Toronto and St. Louis. Pittsburgh has won three of its last five games overall, though the team also recently lost consecutive games against Toronto during that stretch. The Pirates have generally played well at keeping games competitive lately, particularly in lower-scoring matchups.
The Pirates are batting .249 with 258 runs, 467 hits, 56 home runs, a .331 on-base percentage, and a .386 slugging percentage. Pittsburgh’s pitching staff has produced a 3.79 ERA, a 1.23 WHIP, 192 walks, 479 strikeouts, and a .225 opponent batting average. Compared to Chicago, the Pirates hold advantages in batting average, hits, ERA, strikeouts, and opponent batting average.
The biggest strength for Pittsburgh entering this matchup is overall balance. The Pirates have combined steady offensive production with stronger overall pitching numbers than Chicago. Their ability to limit opposing hitters to a .225 average while also generating 479 strikeouts has helped keep the team competitive throughout the season.
Chicago Cubs vs Pittsburgh Pirates Picks and Prediction
Chicago Cubs vs Pittsburgh Pirates Pick
- Pick: Pittsburgh Pirates Moneyline
Pittsburgh enters this game with better recent form and stronger overall pitching numbers. The Pirates recently won over Chicago and have taken three of their last five games, while the Cubs have dropped five straight contests. Pittsburgh also holds advantages in batting average, ERA, strikeouts, and opponent batting average entering this matchup. With Chicago struggling offensively during the losing streak, the Pirates appear to have the edge at home.
Chicago Cubs vs Pittsburgh Pirates Total Pick
- Pick: Take the under if the total is set at 8.5.
I would lean toward the under if the total is set at 8.5 because recent games involving these teams have consistently stayed lower scoring. Pittsburgh recently won over Chicago 2-1, and Chicago scored two runs or fewer in four of its last five losses. Even though both starting pitchers have elevated ERAs, the recent offensive struggles from the Cubs and Pittsburgh’s stronger pitching staff suggest another controlled game environment.
Final Score Prediction: Pittsburgh Pirates 5 – Chicago Cubs 3
This prediction was written before the completion of game play on Tuesday.
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