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Cubs vs Brewers Prediction 5/20/26 MLB Picks Today

Milwaukee Brewers (28-18) vs. Chicago Cubs (29-20)
May 20, 2026 7:40 pm EDT
The Line: Chicago Cubs -120 / Milwaukee Brewers -101; Over/Under: 6.5
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In this article we will formulate a Cubs vs Brewers prediction for this MLB game on Wednesday, May 20th at Wrigley Field in Chicago, Illinois. Let’s take a look at the prediction for this MLB matchup. 

Chicago Cubs Betting Preview

The Chicago Cubs are 29-20 this year after they lost the first two games in this series by scores of 3-9 and 2-5. In game two, Chicago allowed the first five runs in the game and never had a chance in the loss. The Cubs recorded seven hits and they committed one error in the game, while they were led by Hoerner, who went 2-3 with one RBI. Brown allowed seven hits and three earned runs over 5.0 innings for the loss, while Thornton allowed two earned runs in relief. Prior to this series, Chicago lost two out of three against the White Sox and two out of three against the Braves. 

This season, Chicago has a 4.11 ERA with a 1.22 WHIP and a .236 opponent batting average, while they have scored 246 runs with a .245 batting average and a .341 on base percentage. Nico Hoerner has led the Cubs with four home runs and 30 RBIs, while Dansby Swanson has added seven home runs and 27 RBIs. The projected starting pitcher for Chicago is Edward Cabrera, who is 3-1 with a 4.06 ERA and a 1.31 WHIP over 51.0 innings pitched this year. 

Milwaukee Brewers Betting Preview

The Milwaukee Brewers are 28-18 this season after they won game two by a score of 5-2 on Tuesday night. Milwaukee scored in the first inning and never looked back, but they did allow two runs in the eighth to lose the shutout. The Brewers recorded 11 hits and they committed one error in the game, while they were led by Turang, who went 3-4 with one home run and two RBIs. Misiorowski allowed three hits and zero earned runs over 6.0 innings for the win, while Ashby allowed two earned runs in relief. Prior to this series, Milwaukee won two out of three against the Twins and two out of three against the Padres. 

This season, Milwaukee has a 3.25 ERA with a 1.21 WHIP and a .224 opponent batting average, while they have scored 232 runs with a .247 batting average and a .335 on base percentage. Brice Turang has led the Brewers with seven home runs and 29 RBIs, while Jake Bauers has added seven home runs and 28 RBIs. The projected starting pitcher for Milwaukee is Kyle Harrison, who is 4-1 with a 2.09 ERA and a 1.19 WHIP over 38.2 innings pitched this season. 

Why the Chicago Cubs will win

  • The Cubs have won 15 of their last 17 home games.
  • The Brewers have lost each of their last five games as road underdogs against NL Central opponents following a win.
  • The Cubs have covered the run line in six of their last eight games as favorites following a home loss.
  • The Brewers have failed to cover the run line in three of their last four road games following a road win.
  • The Cubs have led after 5 innings in each of their last seven Wednesday games as home favorites.
  • The Cubs have led after 3 innings in each of their last seven Wednesday games as home favorites.

Why the Milwaukee Brewers will win

  • The Brewers have won each of their last four games as underdogs.
  • The Cubs have lost five of their last six games as favorites.
  • The Cubs have failed to cover the run line in each of their last six night games against NL Central opponents.
  • The Brewers have covered the run line in seven of their last eight games against the Cubs.
  • The Brewers have led after 3 innings in five of their last six games against National League opponents.
  • The Brewers have led after 5 innings in each of their last six games against opponents that held a winning record.

Total Runs Facts

  • Each of the Cubs’ last four games as favorites have gone OVER the total runs line.
  • Five of the Brewers’ last six night games as underdogs have gone UNDER the total runs line.
  • The ‘Inning 1 OVER 0.5 runs’ market has hit in six of the last seven games between the Brewers and Cubs.
  • The ‘Inning 1 UNDER 0.5 runs’ market has hit in four of the Brewers’ last five games as underdogs against National League opponents.

Chicago Cubs Player Prop Facts

  • Ian Happ has hit at least one home run in four of the Cubs’ last five Wednesday night games against NL Central opponents that held a winning record.
  • Edward Cabrera has recorded six or more strikeouts in three of his last four appearances with the Cubs as favorites.
  • Seiya Suzuki has recorded at least one hit in each of the Cubs’ last six games against the Brewers.
  • Pete Crow-Armstrong ranks T8th in the league in Steals (12) this season.

Milwaukee Brewers Player Prop Facts

  • Sal Frelick has recorded at least one hit in each of his last 15 road appearances against NL Central opponents.
  • Gary Sanchez has hit a home run in three of his last four road appearances against NL Central opponents that held a winning record.
  • Brice Turang ranks 5th amongst qualified players for On Base Percentage (.413) this season.

Matchup/League Facts

  • The Cubs rank T1st in the league for walks this season (226).
  • The Cubs rank 2nd in the league for on-base percentage this season (.341).
  • The Brewers rank 30th in the league for home runs this season (33).
  • The Brewers rank 1st in the league for home runs allowed this season (35).

Cubs vs Brewers Prediction 

Chicago comes into this matchup on a four game losing streak and they have allowed 31 runs during that span. The Cubs are 18-7 at home this year, while the Brewers are 13-9 on the road. Milwaukee has won four of their last five games and they have allowed three runs or fewer in all four of those wins. The Brewers are starting Harrison, who has allowed two earned runs or fewer in five straight starts, while Cabrera has allowed 3+ earned runs in five straight. Take the Brewers here. 

David Racey's Free Pick: Brewers ML

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David Racey

David started writing about sports in 2015, but sports has been his passion for as long as he can remember. David spends most of his free time watching pretty much anything sports related from Baseball to Tennis and everything in between. David likes to analyze statistics and recent results to form an unbiased opinion on whatever game he is breaking down. Follow David on Twitter at @itsyerboi41

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