After losing back-to-back extra innings games on the south side of Chicago, the Yankees will move north for a Friday matinee matchup at Wrigley Field — as is tradition.
Which is of these historic franchises will prevail in their annual interleague clash? Let’s preview tonight’s contest make a couple picks on the DraftKings Sportsbook.
Yankees vs. Cubs prediction, preview
With almost a full rotation on the IL — one that includes Ben Brown (neck), Edward Cabrera (hamstring) and Cade Horton (elbow) — the Cubs have been leaning on Shota Imanaga as their “ace” in 2026. For the most part, Imanaga has responded, posting a 3.72 ERA ands a 3.63 xERA across 21 starts and 121.0 innings of work. Heck, dating back to June 10, the left-hander sports a flat 2.00 ERA over eight outings. He’s certainly stepped up when needed. With all that said, it’s crucial to note that Imanaga still has one major red flag: His propensity to concede the long ball. The former NPB star is an extreme fly ball archetype, and when that’s paired with a 9.4% opponent barrel rate, you end up allowing 1.64 home runs per nine. A majority of those homers have come at Wrigley Field, too. Fortunately for Imanaga, the wind will be blowing to the east today, not to center.
Another thing working in Imanaga’s favor? The Yankees just aren’t scoring runs at the moment. If not for the ghost runner, New York would have been shutout on Thursday, as the club continues to struggle without the lineup pillars that are Aaron Judge (rib), Giancarlo Stanton (calf) and Cody Bellinger (hamstring). In the 13 games the team has played since the All-Star break, the Yankees rank dead-last in batting average (.202), dead-last in OBP (.270), dead-last in wOBA (.265) and, you guessed it, dead-last in wRC+ (68). There will surely be trades made in the next 72 hours to strengthen this roster, but those don’t matter on Friday. As currently composed, this is one of the worst offenses in the league. Simple as that.
That means it’s up to Will Warren to keep things low-scoring against a Cubs lineup that sits top-three in average (.283), OBP (.365) and wRC+ (126) in the regular season’s second-half. That’s not an easy task. Warren has easily been the least successful of the Yankees’ starters in 2026, pitching to a 4.41 ERA and a 4.58 xERA across 102.0 innings. Things have been especially bleak since June 26, as Warren owns an inflated 7.61 ERA in his six appearances in that span. That includes giving up six earned runs in just three frames to the Phillies this past Sunday. The numbers under the hood aren’t all that encouraging, either. For the season as a whole, Warren’s surrendered a 13th percentile opponent average exit velocity (90.4) and an 18th percentile opponent expected batting average (.266).
Yankees vs. Cubs pick, best bet
Best Bet: Cubs -1.5 (+131)
Seems like a good opportunity to back Chicago on the run line. The Cubs are 30-22 at Wrigley this season and they’ve got their best pitcher on the mound in Shota Imanaga, who owns a 2.00 ERA across his past eight starts. Conversely, the Yankees rank dead-last in batting average (.202), OBP (.270), wOBA (.265) and wRC+ (68) since the All-Star break. They’ve also got the struggling Will Warren toeing the rubber Advantage: Cubs.
