Chicago Cubs vs. Pittsburgh Pirates Prediction and Picks - September 15, 2025
Use Code WWWC Major League Baseball action on Monday evening, and we have a Chicago Cubs vs Pittsburgh Pirates prediction ready to rock and roll. The Cubs enter this game at 85-64 on the year, and they currently hold the top National League Wildcard slot. The Pirates are just playing out the string as they come in at 65-85 and in last place in the NL Central. Read on to see our Cubs vs Pirates prediction.
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Cubs Are Holding Down the Top Wildcard Slot
The Cubs closed out their weekend series with a gritty 4–3 win over the Rays on Sunday, rallying from a 3–1 deficit behind clutch hitting from Nico Hoerner and Ian Happ. Hoerner delivered a go-ahead two-run double in the seventh and finished 2-for-4 with three RBIs, while Happ launched his 22nd homer of the season to spark the comeback. Javier Assad earned the win in relief, tossing 2.1 scoreless innings, and Andrew Kittredge locked down his fifth save with a three-strikeout ninth. Chicago has now won four of its last five and sits 5.5 games behind Milwaukee in the NL Central.
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Offensively, the Cubs are clicking. Pete Crow-Armstrong leads the team with 28 home runs and 87 RBIs, while Seiya Suzuki has driven in 91 runs and extended his hitting streak to six games. Hoerner enters Monday batting .299 and riding a nine-game hit streak, hitting .410 over his last 10 games. Chicago ranks top 10 in MLB in home runs (200), slugging (.427), and runs scored (727), and they’ve covered the run line in five of their last six road games against Pittsburgh.
Jameson Taillon (9–6, 4.15 ERA) gets the start Monday, looking for his 10th win of the season. He’s posted a 1.11 WHIP and held opponents to a .236 average across 110.2 innings. Taillon has already faced the Pirates once this season, allowing just two runs over 6.1 innings with a 0.947 WHIP. With playoff positioning in play and the Cubs trending upward, Taillon will be leaned on to deliver another quality start against a struggling Pittsburgh lineup.
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Pirates Have Lost Nine Of Ten
The Pirates dropped Sunday’s series finale to Washington 4–3, blowing an early 3–0 lead and falling for the ninth time in their last ten games. Nick Gonzales drove in two runs in the first, but the offense went quiet from there—managing just five hits and striking out nine times. Jared Jones lasted 4.1 innings, allowing three earned runs, and Isaac Mattson took the loss in relief. Pittsburgh has now lost four straight series and sits last in the NL Central, 26 games behind Milwaukee.
This recent stretch has exposed the team’s offensive struggles. The Pirates have scored two runs or fewer in six of their last ten games and rank dead last in MLB in slugging (.349) and home runs (107). Bryan Reynolds and Oneil Cruz remain the primary threats, but the lineup has failed to sustain rallies or capitalize on scoring chances. Andrew McCutchen and Spencer Horwitz have shown flashes, yet the team has gone just 3-for-28 with runners in scoring position over the last four games.
Braxton Ashcraft (4–2, 2.47 ERA) gets the start Monday, hoping to stabilize a rotation that’s been inconsistent during the skid. Ashcraft has allowed two runs or fewer in 22 of his 23 MLB outings and enters with a .225 opponent batting average and 8.6 K/9. He’s yet to record a quality start but has been effective in short bursts. Against a Cubs lineup that’s top 10 in slugging and runs scored, Ashcraft will need to work efficiently and avoid early traffic to keep Pittsburgh competitive.
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Chicago Cubs vs Pittsburgh Pirates Pick
Cubs vs Pirates Moneyline Pick
- Chicago -135 (5 Units)
Chicago is well-positioned to take Monday’s matchup behind Jameson Taillon, who’s held opponents to a .236 average and posted a 1.11 WHIP across 110 innings this season. He’s already handled the Pirates once this year, allowing just two runs over 6.1 innings with a 0.947 WHIP and .182 opponent average. The Cubs enter with momentum after Sunday’s 4–3 comeback win over Tampa Bay and have won four of their last five. Offensively, Nico Hoerner is red-hot with a .410 average over his last 10 games, and Pete Crow-Armstrong leads the team with 28 homers. Against a Pirates lineup that ranks 30th in slugging and home runs, Chicago has the edge in both firepower and form.
Pittsburgh has dropped nine of its last ten and continues to struggle generating offense, scoring just 3.6 runs per game on the season. Braxton Ashcraft has been effective in short outings, but he’s yet to record a quality start and faces a Cubs team that ranks top 10 in runs, slugging, and home runs. Chicago has covered the run line in five of its last six road games against Pittsburgh, and with playoff positioning still in play, expect a focused effort from a team that’s 52–28 when favored by -135 or more. If Taillon delivers another efficient outing and the top half of the lineup stays hot, the Cubs should control this one from start to finish.
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Cubs vs Pirates Over/Under Pick
- Under 8 (3 Units)
Under 8 is well-supported in Monday’s Cubs–Pirates matchup, with both teams trending toward low-scoring outcomes. Jameson Taillon has held opponents to three runs or fewer in four of his last five starts and already limited Pittsburgh to two runs over 6.1 innings earlier this season. Braxton Ashcraft enters with a 2.47 ERA and has allowed two or fewer earned runs in 22 of 23 outings, though he’s yet to work deep into games. The Pirates have scored just 3.2 runs per game during their 9-of-10 skid, and the Cubs have hit the under in six of their last ten. With two efficient starters and a struggling Pittsburgh offense, this profiles as a 4–2 type finish that stays under the number.
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