Pick details
| MATCHUP | Milwaukee Brewers | Chicago Cubs |
|---|---|---|
| Team Records | 85-52 | 77-60 |
| Spread | -1.5 149 | +1.5 -181 |
| Moneyline | -106 | -114 |
| Total | Over 9.5 (-107) | Under 9.5 (-113) |
| Where | Wrigley Field, Chicago, Illinois | |
| When | Monday, August 31, 2026 | |
| Time | 07:40 PM EDT | |
| TV | MLB.TV | |
Milwaukee Brewers Betting Preview
The Milwaukee Brewers are 85-52 on the year and play the Reds and Cubs next. The Milwaukee Brewers are batting .255 on the season, have a .338 OBP, and have a .397 slugging percentage. The Milwaukee Brewers’ pitching staff has a 3.37 ERA and a 1.16 WHIP. William Contreras leads the Milwaukee Brewers with 131 hits and 70 RBI, while Brice Turang and Jackson Chourio have combined for 244 hits and 135 RBI.
Kyle Harrison gets the ball for the Milwaukee Brewers, and he is 10-3 with a 2.79 ERA and 127 strikeouts this season. Harrison is 1-0 with a 1.38 ERA and 22 strikeouts in his career against the Chicago Cubs.
Chicago Cubs Betting Preview
The Chicago Cubs are 77-60 on the year and play the Marlins and Brewers next. The Chicago Cubs are batting .251 on the season and have a .339 OBP and a .428 slugging percentage. The Chicago Cubs’ pitching staff has a 4.14 ERA and a 1.26 WHIP. Pete Crow-Armstrong leads the Chicago Cubs with 149 hits and 91 RBI, while Alex Bregman and Nico Hoerner have combined for 276 hits and 134 RBI.
Clay Holmes gets the ball for the Chicago Cubs, and he is 5-6 with a 2.26 ERA and 55 strikeouts this season. Holmes is 1-3 with a 5.96 ERA and 24 strikeouts in his career against the Milwaukee Brewers.
Why the Chicago Cubs will win
- The Cubs have won seven of their last eight games at Wrigley Field following a home loss.
- The Brewers have lost four of their last five night games against teams that held a winning record.
- The Cubs have covered the run line in seven of their last eight games at Wrigley Field following a home loss.
- The Brewers have failed to cover the run line in five of their last six night games against NL opponents that held a winning record.
- The Brewers have trailed after 5 innings in three of their last four night games against NL opponents that held a winning record.
Why the Milwaukee Brewers will win
- The Brewers have won each of their last five games as underdogs against the Cubs following a loss.
- The Cubs have lost four of their last five games as favorites against NL Central opponents.
- The Brewers have covered the run line in each of their last seven games as road underdogs against the Cubs following a loss.
- The Cubs have failed to cover the run line in each of their last eight Monday night games as home favorites against NL Central opponents.
- The Cubs have trailed after 3 innings in six of their last eight games at Wrigley Field against NL Central opponents that held a winning record.
- The Brewers have led after 5 innings in four of their last five games.

Total Runs Facts
- Each of the Cubs’ last five home games against NL Central opponents have gone OVER the total runs line.
- Six of the Brewers’ last seven games as underdogs have gone OVER the total runs line.
- There has been at least one run scored in the first inning in eight of the Cubs’ last nine games as home favorites against NL opponents.
- There has been no run scored during the first inning in 13 of the Brewers’ last 15 night games against NL opponents.
Chicago Cubs Player Prop Facts
- Pete Crow-Armstrong has hit at least one home run in three of the Cubs’ last four home games against NL Central opponents.
- Clay Holmes has recorded five or more strikeouts in three of his last four appearances against NL opponents.
- Ian Happ has recorded at least one hit in each of the Cubs’ last nine night games.
- Pete Crow-Armstrong ranks 2nd amongst qualified players for Slugging Percentage (.577) this season.
Milwaukee Brewers Player Prop Facts
- Jake Bauers has hit a home run in two of the Brewers’ last three games as underdogs against the Cubs.
- Kyle Harrison has recorded six or more strikeouts in three of his last four appearances with the Brewers as road underdogs.
- Andrew Vaughn has recorded at least one hit in each of the Brewers’ last eight games against NL opponents.
Matchup/League Facts
- The Cubs rank 1st in the league for on-base percentage this season (.339).
- The Cubs rank 1st in the league for walks this season (576).
- The Brewers rank 2nd in the league for walks this season (566).
- The Brewers rank 2nd in the league for ERA this season (3.37).
Milwaukee Brewers vs Chicago Cubs Prediction
You can make a case for either team or either pitcher, but I have to lean toward the Brewers and the pitcher with Harrison on the mound. As good as Holmes has been, the Brewers are playing the better baseball at the moment, and Harrison has allowed 19 hits and 4 earned runs in his last 19.2 innings. You’re not going to get the Brewers at this price often the rest of the regular season. I’ll take it. Give me the Brewers in an intriguing Monday MLB contest.
Randy Chambers's Pick: Milwaukee Brewers


