With a little under two weeks left in the regular season, the Cubs don’t really have much to play for. The Brewers remain five games up in the National League Central, while Chicago itself is leading San Diego by five games in the race for the top Wild Card spot. Translation: The Cubs are about the only team in MLB that knows exactly what seed it’ll have when the postseason starts in October.
Still, that doesn’t mean Chicago won’t want to beat Pittsburgh on Wednesday. Let’s preview this divisional matchup with the help of some of those odds and lines on the DraftKings Sportsbook.
Cubs vs. Pirates prediction, preview
If there is something that the Cubs’ brass would like to see before the playoffs begin, it would simply be Matthew Boyd getting back on track. The All-Star seemed almost unhittable at one point or another this season, yet Boyd is coming back down to Earth at the wrong time. Over Boyd’s last five starts, the left-hander is in possession of a 5.97 ERA and a 5.17 FIP. It’s a stretch where the veteran has been a little unlucky with a stand rate below 65%, yet Boyd’s issues are primarily about home runs. Despite a 0.86 GB/FB ratio, Boyd had done a good job a majority of 2025 keeping the ball in the park. Heck, across June and July, Boyd only allowed four total opponent long balls. He’s now surrendered five in his last five outings. Add in a diminishing strikeout rate and you can see the red flags beginning to appear.
That said, Boyd possesses a 3.05 ERA over 171.1 innings of work. In general, he’s been fantastic. Plus, if there was a matchup designed to get a pitcher back in the groove, it would be the Pirates. Pittsburgh hasn’t been able to score runs all year long, but things have been especially bleak so far in September. Since the beginning of the month, the Pirates are slashing .188/.277/.288 as a team with an MLB-low .256 wOBA. No club has hit fewer home runs the past 16 days (7). This Pittsburgh lineup is underwhelming in every sense of the word.
The Pirates’ rotation is a different story. Anchored by Paul Skenes and Bubba Chandler, Pittsburgh’s collection of young arm talent is the thing that could propel the organization back to something resembling success in 2026 or 2027. Johan Oviedo is now auditioning to be apart of that — and so far its’s going pretty well. The RHP struggled in his first start of the season back in early August, yet Oviedo has been on fire ever since, registering a 2.19 ERA with a 26.0% strikeout rate in his last five appearances. It’s a span of time where Oviedo has held opponents to a .248 wOBA over 24.2 innings. Not too shabby at all.
Cubs vs. Pirates pick, best bet
Best Bet: Under 8 (-119)
58.5% of Pirates games have gone under in 2025 — the second-highest rate in the league. The team simply can not score runs, and a 59 wRC+ in September backs that claim up.
