Chicago Cubs vs Pittsburgh Pirates Pick – 9/15/2025
The Chicago Cubs and Pittsburgh Pirates will play the first game in a three-game series on Monday night at PNC Park in Pittsburgh. Chicago is pushing to lock in postseason positioning, while Pittsburgh is simply trying to play the role of spoiler at home. Here, I take a closer look at this game in the betting markets and make my Cubs vs Pirates prediction for Monday night.
Our Cubs vs Pirates Pick
- Pick: Cubs Moneyline
- Confidence: 4/5
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Game Snapshot
- Matchup: Chicago Cubs vs Pittsburgh Pirates
- Date and Time: Monday, September 15, 6:40 p.m. ET
- Starting Pitchers: Jameson Taillon vs Braxton Ashcraft
- Stadium: PNC Park, Pittsburgh, PA
- Broadcast: MLB Network
Key Storylines
Pitching matchup
Jameson Taillon will get the ball for the Cubs to start this game. Taillon hasn’t been overly impressive for the Cubs this year. He is 9-6 and has a 4.15 ERA for the season. But Taillon has given up two or fewer runs in four straight starts and he will look to continue trending in the right direction in this start.
It will be Braxton Ashcraft getting the ball for the Pirates in this game. Ashcraft has pitched well in 2025 with a 4-2 record and 2.47 ERA. Ashcraft has allowed one run or less in six straight starts and he will try to keep his team in this game as well.
Recent team streaks
- The Cubs have won four of their last five games going into Monday’s series opener with the Pirates.
- Pittsburgh has dropped four of their last five games going into tonight’s action.
Best Player Props
| Player | Market | Suggested Play |
|---|---|---|
| Braxton Ashcraft | Strikeouts | Under 4.5 K |
| Jameson Taillon | Strikeouts | Over 5.5 K |
| Pete Crow-Armstrong | Total Bases | Over 1.5 TB |
| Bryan Reynolds | Total Bases | Over 1.5 TB |
Betting Trends & H2H
- The Cubs hold a 7-3 lead in the season series against the Pirates this year.
- Chicago has won four of the last five games between these teams entering Monday night.
- The Pirates are 2-8 over their last 10 games.
- Chicago is 39-35 on the road so far this season.
- Pittsburgh is 42-33 at home for the year.
Cubs vs Pirates Model Projection
Score Projection: Cubs 5 – Pirates 3
Win Probability: Cubs 55%, Pirates 45%
Final Thoughts
The Chicago Cubs should be able to get the job done in this contest against the Pittsburgh Pirates on the road. The Cubbies are more consistent at the plate and should be able to get after the Pirates bullpen once Ashcraft exits this contest. I expect Chicago to win this game by two runs, though I will be taking them on the moneyline instead of laying the runline.
