Milwaukee Brewers vs Chicago Cubs Picks and Prediction for Wednesday May 20 2026
The Milwaukee Brewers travel to face the Chicago Cubs on Wednesday May 20, 2026, at Wrigley Field in Chicago, Illinois. First pitch is scheduled for 7:40 PM ET with coverage on ESPN Unlmtd and MLB.TV. At the time of this writing the odds were not released. Be sure to check out our free MLB picks.
Starting Pitchers
Kyle Harrison is expected to start for Milwaukee in this matchup. The left-hander enters with a 4-1 record, a 2.09 ERA, and a 1.19 WHIP across 38.2 innings pitched. He has allowed 33 hits while recording 48 strikeouts and issuing 13 walks with only three home runs surrendered. Chicago is expected to counter with Edward Cabrera, who enters with a 3-1 record, a 4.06 ERA, and a 1.31 WHIP over 51.0 innings. He has allowed 49 hits while striking out 45 batters and walking 18 while allowing eight home runs.
Brewers Carrying Momentum Into Rivalry Matchup
Milwaukee enters Wednesday with a 27-18 overall record and a 12-9 road record. The Brewers recently won over Chicago 9-3 after recently winning over Minnesota by scores of 2-1 and 3-2. Milwaukee also recently lost to Minnesota 5-4 but recently won over San Diego 7-1. The Brewers have won four of their last five games and continue playing strong baseball entering another divisional contest.
Milwaukee is batting .246 as a team with 227 runs scored and 373 hits this season. The Brewers have hit 32 home runs while posting a .335 on-base percentage and a .366 slugging percentage. On the mound, Milwaukee owns a 3.28 ERA and a 1.21 WHIP while limiting opponents to a .224 batting average. The Brewers have recorded 436 strikeouts while issuing 155 walks this season.
Sign Up Get $30 Premium Picks Credit + Exclusive Offers
Subscribe Now
One major strength for Milwaukee entering this matchup is pitching efficiency. The Brewers carry the lower ERA, lower WHIP, and better opponent batting average compared to Chicago. Milwaukee has also consistently generated strikeouts and has allowed three runs or fewer in three of its last four victories.
Cubs Looking to Recover at Home
Chicago enters the matchup with a 29-19 overall record and an impressive 18-6 home record. The Cubs recently lost to Milwaukee 9-3 after recently losing to the White Sox by scores of 9-8 in 10 innings and 8-3. Chicago did recently win over the White Sox 10-5 and recently won over Atlanta 2-0 before this current rough stretch. Despite the recent losses, the Cubs continue to hold one of the stronger records among the teams playing Wednesday.
Chicago is batting .246 as a team with 244 runs scored and 401 hits this season. The Cubs have hit 58 home runs while posting a .342 on-base percentage and a .405 slugging percentage. On the mound, Chicago owns a 4.10 ERA and a 1.22 WHIP while opponents are batting .235 against the pitching staff. The Cubs have recorded 386 strikeouts and issued 145 walks this season.
One important strength for Chicago is offensive production. The Cubs have scored more runs, recorded more hits, and hit significantly more home runs than Milwaukee this season. Chicago has also been outstanding at home with an 18-6 record at Wrigley Field, giving the Cubs a strong opportunity to respond after the loss in the series opener.
Milwaukee Brewers vs Chicago Cubs Picks and Prediction
Milwaukee Brewers vs Chicago Cubs Pick
- Pick: Milwaukee Brewers Moneyline
Milwaukee enters this matchup with stronger recent momentum and the advantage in starting pitching. The Brewers have won four of their last five games and recently defeated Chicago 9-3 in the series opener. Milwaukee also owns the lower ERA, lower WHIP, and better opponent batting average entering Wednesday. Kyle Harrison has been excellent this season with a 2.09 ERA, while Chicago’s starter enters with an ERA above 4.00. Even with Chicago’s strong home record, Milwaukee’s pitching edge gives the Brewers value in this matchup.
Milwaukee Brewers vs Chicago Cubs Total Pick
- Pick: Take the under if the total is set at 8
I would lean toward the under because Milwaukee’s pitching staff has consistently limited opponents this season with a 3.28 ERA and a .224 opponent batting average. The Brewers have also played several low-scoring games recently, including 3-2, 2-1, and 7-1 results during the last week. While Chicago has strong offensive numbers overall, Milwaukee’s pitching consistency and strong starting pitching matchup point toward a more controlled scoring environment.
Final Score Prediction: Milwaukee Brewers 5 – Chicago Cubs 3
This prediction was written before the completion of game play on Tuesday.
Never Tried Picks and Parlays? Now Is Your Chance
- Get your first daily picks package for ONLY $1 using coupon code BUCK
- If the pick loses, we credit your account with 3 Flex Picks
- If the pick wins, we still give you 1 Flex Pick on the house
- Win or lose, you walk away ahead. One dollar. No catch.
Spend $10 Get 200 in Bonus Picks
$200 in No Sweat Entries + A Free Pick
Get 100% on any coins purchase up to $100
