Milwaukee Brewers @ Chicago Cubs Player Props, Picks and Predictions - 8/21/2025 2:20 PM EDT

We have your Milwaukee Brewers @ Chicago Cubs prop betting and game preview needs covered as the Milwaukee Brewers hit the road to face the Chicago Cubs.

Milwaukee Brewers @ Chicago Cubs Pick

Best Moneyline Odds: Chicago Cubs -140 (Caesars)
Best Spread Odds: Chicago Cubs -1.0 (+106) (BetRivers)
Best Total Odds: Over 6.5 (-118) (BetMGM)

Game Info

Date: 2025-08-21
Time: 2:20 PM EDT
Location: Wrigley Field, Chicago, Illinois
TV: MLB Network, FDSN Wisconsin, Marquee Sports Network

Milwaukee Brewers @ Chicago Cubs Preview

The Milwaukee Brewers (79-48) travel to Wrigley Field to take on the Chicago Cubs (73-54) in what marks the fifth head-to-head matchup between these two NL Central rivals in just four days. The Brewers, despite leading the NL Central, are looking to snap a three-game losing streak, their first since early May. The Cubs, meanwhile, have found their stride, winning their last three games, including a tight 4-3 victory over the Brewers yesterday, and have cut Milwaukee's division lead to six games.

On the mound, the Brewers will send Quinn Priester (11-2, 3.48 ERA) to the hill. While Priester boasts an impressive win-loss record, his underlying metrics, including an xERA of 3.82, suggest he may be due for some regression. Notably, he has struggled against the Cubs this season, posting a 7.31 ERA in three previous appearances. For the Cubs, left-hander Shota Imanaga (8-5, 3.06 ERA) gets the start. Imanaga has been in excellent form this month, recording a 2.25 ERA across three starts with 22 strikeouts and just two walks. He also secured a win against the Brewers last month, giving the Cubs a clear pitching advantage in this contest.

Offensively, the Brewers have shown strong numbers this season, ranking second in the league in both batting average (.258) and on-base percentage (.331). Their pitching staff also holds a respectable 3.58 ERA, placing them fourth in the league, with a .229 batting average against, ranking third. Key players for Milwaukee include Christian Yelich, who has tallied 26 home runs and 87 RBIs, and Brice Turang, batting .284. The Cubs counter with a potent offense of their own, boasting a team slugging percentage ranked fifth in the league and 173 home runs, placing them seventh overall. Players like Seiya Suzuki and Michael Busch will be crucial for the Cubs' continued offensive success.

Historic Head-to-Head Stats and Analysis

The recent head-to-head history between the Milwaukee Brewers and the Chicago Cubs indicates a tightly contested rivalry. In their most recent 10 matchups, spanning from May 3, 2025, to August 19, 2025, both teams have secured 5 wins each. This even split suggests that these games are often decided by fine margins, with neither team holding a significant historical edge over the other in recent memory. The last game played on August 20, 2025, saw the Chicago Cubs emerge victorious with a 4-3 scoreline.

Pick: Chicago Cubs Moneyline

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The Chicago Cubs are the favored pick in this matchup, and for good reason. Multiple analytical models and sharp betting insights point towards a Cubs victory, with their win probability hovering around 56.83%. The pitching matchup heavily favors the Cubs, as Shota Imanaga has been in stellar form, especially in August, while Brewers' starter Quinn Priester has struggled against Chicago this season. The Cubs have also demonstrated strong momentum, winning their last three games and taking control of this five-game series. With the home-field advantage at Wrigley Field and a clear edge on the mound, the Cubs are well-positioned to extend their winning streak and secure another victory against the Brewers. You can find the best odds for the Cubs Moneyline at -140 with Caesars.

Top Player Prop Picks

Sal Frelick (Milwaukee Brewers) - Over 0.5 Bases

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Sal Frelick has been consistently hitting the over on his bases prop, making him a strong candidate for this pick. He has hit the over in 80% of his last 5 games and 80% of his last 10 games, with a 75% hit rate over his last 20 outings. His season average for bases is 1.52, well above the 0.5 line. Furthermore, when playing as the visitor in 2025, he has hit the over in 72.22% of his games. Against the Cubs in 2025, he has hit the over in 66.67% of his appearances. You can bet on Sal Frelick Over 0.5 Bases at -170 odds with Caesars.

Brice Turang (Milwaukee Brewers) - Over 0.5 Hits

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Brice Turang presents another compelling player prop. He has hit the over on his hits prop in 80% of his last 5 games, 80% of his last 10 games, and 75% of his last 20 games. His season average for hits is 1.07, comfortably above the 0.5 line. Turang has also performed well against the Cubs in 2025, hitting the over in 75% of his matchups against them. As a visitor in 2025, he has hit the over in 70.97% of his games. You can find Brice Turang Over 0.5 Hits at -150 odds with BetRivers.

Owen Caissie (Chicago Cubs) - Over 0.5 Hits

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Owen Caissie, playing at home for the Cubs, is a strong pick for hits. He has hit the over on his hits prop in 60% of his last 5 games and 50% for the season. More importantly, he has a 75% hit rate against the Brewers in 2025 and a 60% hit rate in home games this season. His season average for hits is 0.67, which is above the 0.5 line. You can bet on Owen Caissie Over 0.5 Hits at -150 odds with BetRivers.