Milwaukee Brewers vs Chicago Cubs Picks and Prediction for Monday August 31 2026

The Milwaukee Brewers travel to Wrigley Field to face the Chicago Cubs on Monday night in Chicago, Illinois. First pitch is scheduled for 7:40 PM ET on August 31, with MLB.TV providing the coverage. Milwaukee enters at 85-51 overall and 38-27 on the road, while Chicago is 77-59 overall and 39-28 at home. The Brewers lead the season series 4-2 and also bring a four-game winning streak into this matchup. ESPN's Matchup Predictor gives Chicago a 55.5% chance to win compared with 44.5% for Milwaukee. At the time of this writing the odds were not released. Before placing any wagers on Monday's matchup, check out our free MLB picks for more baseball predictions and betting analysis.

Starting Pitchers

Milwaukee is scheduled to start Kyle Harrison, who enters at 10-3 with a 2.79 ERA and 1.12 WHIP through 103.1 innings. Harrison has allowed 89 hits while recording 127 strikeouts against 27 walks and has surrendered 14 home runs. Chicago counters with Clay Holmes, who is 5-6 with a 2.26 ERA and 1.06 WHIP through 75.2 innings. Holmes has allowed 55 hits while striking out 55 against 25 walks and has surrendered only four home runs. Both starters bring strong numbers into this matchup, with Chicago holding the ERA and WHIP edge while Milwaukee's starter has the larger workload and much higher strikeout total.

Brewers Bring the Better Overall Form

Milwaukee enters Monday with the best record in the National League Central at 85-51. The Brewers are also 38-27 away from home and have won four straight completed games. Their last four victories have come by scores of 5-3, 6-1, 8-2 and 8-1, giving them a strong combination of recent offense and run prevention.

The Brewers are batting .256 as a team with 679 runs, 1,178 hits and 125 home runs. They own a .338 on-base percentage and .398 slugging percentage. Milwaukee has not relied heavily on home-run power, but the offense consistently gets runners on base and has produced 679 runs through 136 games.

Pitching is the club's biggest statistical strength. Milwaukee owns a 3.36 team ERA and 1.16 WHIP while holding opposing hitters to a .219 batting average. The staff has issued 426 walks while recording 1,312 strikeouts. Those numbers are significantly better than Chicago's season pitching marks.

The Brewers have also controlled this head-to-head matchup, winning four of the first six meetings. Three of those victories came by margins of at least four runs, and Milwaukee has allowed Chicago three runs or fewer in four of the six meetings.

Cubs Counter With a Dangerous Offense

Chicago enters Monday at 77-59 and remains second in the National League Central, eight games behind Milwaukee. The Cubs are 2-3 over their last five completed games, but they are coming off a 17-5 victory and have scored 25 runs over their last two contests.

The Cubs are batting .251 with 720 runs, 1,176 hits and 185 home runs. They carry a .339 on-base percentage and .428 slugging percentage. Chicago has scored 41 more runs than Milwaukee and owns a substantial power advantage, hitting 60 more home runs.

The pitching staff has not been nearly as effective. Chicago carries a 4.12 ERA and 1.25 WHIP while allowing opponents to bat .243. The staff has issued 408 walks while recording 1,046 strikeouts. That creates a clear overall pitching advantage for Milwaukee.

Chicago does have an excellent 39-28 home record and a scheduled starter with outstanding numbers, which makes this a difficult game to price. Still, the Cubs have lost three of their last five and face a Milwaukee team that has been more consistent over the full season and much stronger on the mound.

Milwaukee Brewers vs Chicago Cubs Picks and Prediction

Pick: Milwaukee Brewers Moneyline

Milwaukee is the preferred side despite ESPN's predictor leaning toward Chicago. The Brewers own the better overall record, the stronger team pitching numbers and a 4-2 advantage in the season series. They also enter on a four-game winning streak and have allowed only seven total runs across those four victories. Chicago's offense is more powerful, and its scheduled starter has been excellent, but Milwaukee's balance and recent form make the road side more attractive. Take Milwaukee on the moneyline once the market becomes available.

Pick: Under 8.5

The starting matchup points toward a lower-scoring game. Milwaukee's scheduled starter owns a 2.79 ERA and 1.12 WHIP, while Chicago's starter carries a 2.26 ERA and 1.06 WHIP. Milwaukee also owns a 3.36 team ERA and has held opponents to three runs or fewer in each of its last four completed games. Chicago's recent offensive explosion creates some risk, but the strength of both starters makes the Under the better position at this target number. Take the Under if the total is set at 8.5 or higher.

Final Picks: Milwaukee Brewers Moneyline and Under 8.5

This preview was completed before play on Sunday. Starting pitchers, betting lines and other game information are subject to change before the game begins.