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Read Article Cubs vs. Pirates prediction: Why Pittsburgh is favored to win Wednesday's MLB matchup [5/27/2026]
Updated: | First published:
Written by Dave Garofolo, Content Producer
Get Chicago Cubs vs Pittsburgh Pirates predictions for MLB Wednesday.
The Pittsburgh Pirates and Chicago Cubs are scheduled to meet in MLB action at PNC Park on Wednesday, starting at 6:40 PM ET.
The Pirates will start Bubba Chandler (1-6, 4.60 ERA), while the Cubs have opted for Jameson Taillon (2-4, 5.20 ERA).
Based on the latest simulation results, Dimers' proven MLB model gives the Pirates a slight edge with a 52% win probability over the Cubs.
This article offers further insights into Wednesday's Cubs vs. Pirates matchup, including best bets and picks.
Cubs vs. Pirates prediction: Who will win and cover?
Using trusted machine learning and data analysis, we have simulated the outcome of Wednesday's MLB game between the Cubs and Pirates, forming part of our MLB predictions coverage.
Our leading predictive model currently gives the Pirates a 52% chance of beating the Cubs.
According to our model, the Cubs (+1.5) have a 64% chance of covering the run line, while the over/under total of nine runs has an equal 50-50 chance of hitting.
Cubs vs. Pirates odds [5/27/2026]
We have sourced the best MLB odds in America for this game, which are listed here:
| Bet Type | Cubs | Pirates |
|---|---|---|
| Run Line | +1.5 (-200) | -1.5 (+165) |
| Moneyline | +105 | -122 |
| Total | o9 (-102) | u9 (-118) |
All odds are correct at the time of publication and are subject to change.
Cubs vs. Pirates picks and best bet
After matching our predictions against the best current odds, we can reveal our picks for each of the major markets. Plus, find our best bet for the game below:
| Bet Type | Pick | Bet Now |
|---|---|---|
| Run Line | Pirates -1.5 | +165 |
| Moneyline | Cubs | +105 |
| Total | Over 9 | -102 |
According to our MLB best bets, the top play to make on this game is Over 9 total runs.
These picks are based on our probabilities matched against the implied probabilities from the sportsbook odds.
Cubs vs. Pirates game-day updates and essential details
Wednesday's MLB game between the Pirates and Cubs at PNC Park is scheduled to begin at 6:40 PM ET.
- Who: Chicago Cubs vs. Pittsburgh Pirates
- Date: Wednesday, May 27, 2026
- Time: 6:40 PM ET/3:40PM PT
- Venue: PNC Park
Conclusion
We predict the Pirates, with a 52% win probability, will likely beat the Cubs in Wednesday's MLB matchup.
Additional tools and information for betting safely can be found in our Responsible Gambling hub.
Dave Garofolo uses sophisticated AI-driven analytics to make predictions and evaluate player performances in the NBA, MLB, NFL, NHL, NCAAM, and PGA TOUR tournaments, crafting insightful game and prop previews.
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