Wednesday’s full MLB slate features 15 matchups on May 27, 2026, with start times spanning from 1:07 PM ET to 10:10 PM ET.
I like a pair of teams playing in the evening on Wednesday. Both teams are small favorites.
Can 23-year-old Pirates righty Bubba Chandler pitch well enough to earn his second win of the season on Wednesday? Will Braves starter Bryce Elder improve his record to 5-2 in a road matchup with the Red Sox?
I'll make picks for both games below. Read on for our Wednesday MLB Predictions May 27 article.
MLB Prediction Game 1
CUBS VS PIRATES DATE, TIME & HOW TO WATCH | |
|---|---|
| Where | PNC PARK, PITTSBURGH, PA |
| When | WEDNESDAY, MAY 27, 2026, 6:40 PM ET |
| TV | MLB.TV |
CUBS VS PIRATES ODDS | |||
|---|---|---|---|
| Run Line | Moneyline | Total | |
| CUBS | 1.5 (-210) | -103 | U 9.0 (+105) |
| PIRATES | -1.5 (+175) | -117 | O 9.0 (-125) |
Odds change, get the latest MLB Odds - Futures - Props
CUBS VS PIRATES WHO IS THE PUBLIC BETTING? | |||
|---|---|---|---|
| CUBS | 31% | 69% | PIRATES |
See the latest MLB Public Betting Splits and make smarter wagers!
Chicago Cubs at Pittsburgh Pirates May 27 MLB Prediction
The Pittsburgh Pirates should defeat the Chicago Cubs outright as Wednesday night's money line home favorites by capitalizing on Chicago's shaky recent play.
Pittsburgh leverages a solid home-field advantage, sitting 15-13 straight up as the home team, and dominates rivals with a 13-8 straight up record in division games this year. Furthermore, the Pirates hold a 22-21 straight up mark in National League contests this season while having recent success, going 5-3 straight up in their last 8 games overall.
Conversely, Chicago brings severe struggles into PNC Park. The Cubs have lost 10 straight games and sit at a dismal 2-14 straight up in their last 16 games overall. Take the Pirates here.
Pick: Pittsburgh Pirates -117
MLB Prediction Game 2
BRAVES VS RED SOX DATE, TIME & HOW TO WATCH | |
|---|---|
| Where | FENWAY PARK, BOSTON, MA |
| When | WEDNESDAY, MAY 27, 2026, 6:45 PM ET |
| TV | MLB.TV |
BRAVES VS RED SOX ODDS | |||
|---|---|---|---|
| Run Line | Moneyline | Total | |
| BRAVES | -1.5 (+135) | -119 | U 8.0 (+102) |
| RED SOX | 1.5 (-160) | -101 | O 8.0 (-110) |
BRAVES VS RED SOX WHO IS THE PUBLIC BETTING? | |||
|---|---|---|---|
| BRAVES | 79% | 21% | RED SOX |
Atlanta Braves at Boston Red Sox May 27 MLB Prediction
The Atlanta Braves are well-positioned to secure an outright victory on Wednesday as money line road favorites against the Boston Red Sox. The Braves will by relying on some favorable situational trends.
Atlanta excels at sustaining momentum, boasting a 22-14 straight up record following a win in 2026. The Braves also overpower American League opponents, going 14-8 straight up in interleague games this year. They consistently conquer hostile environments with a stellar 20-8 straight up mark as the road team, and they handle expectations perfectly, sitting 29-15 straight up as a favorite this season.
Furthermore, starting pitcher Bryce Elder gives Atlanta a significant edge on the mound. The Braves boast a 7-4 straight up record across his 11 starts this year. Take the NL-leading Braves at Fenway on Wednesday.
Pick: Atlanta Braves -119
Today's MLB Predictions
- Pittsburgh Pirates -117
- Atlanta Braves -119