Walk-Off Wagers: MLB Best Bets Today (Predictions for Brewers-Cubs, Orioles-Red Sox, Paul Skenes)

Breaking down the best bets for the MLB action on Monday, Aug. 18, including a wager involving Paul Skenes.

The UNDER in the Pittsburgh Pirates' game may be a great bet with starting pitcher Paul Skenes getting the start. / Benny Sieu-Imagn Images

Monday’s Major League Baseball action is headlined by a matchup between the two best teams in the NL Central — the Milwaukee Brewers and Chicago Cubs.

These two playoff contenders will play a doubleheader to open the day’s action, and the Brewers are looking to build on their MLB-best record. 

Meanwhile, the Cubbies hold the top spot in the NL wild card race and are one of many teams in the mix for a playoff spot this season.

With so much at stake over the next few weeks in MLB, why don’t we bet on some of the action for Monday’s slate?

I’m eyeing a prediction for Game 1 of the Brewers-Cubs doubleheader, as well as an upset in an AL East matchup. 

Let’s dive into each of these picks – and more – for Aug. 18.

MLB Best Bets for Monday, Aug. 18

Odds via DraftKings Sportsbook

• Milwaukee Brewers Moneyline (+108) vs. Chicago Cubs
• Baltimore Orioles Moneyline (+104) vs. Boston Red Sox
• Toronto Blue Jays-Pittsburgh Pirates UNDER 7 (-107)

Milwaukee Brewers Moneyline (+108) vs. Chicago Cubs

Game 1 between the Brewers and Cubs features a pretty strong pitching matchup, as Milwaukee’s ace – Freddy Peralta – takes on up-and-coming righty Cade Horton. 

Horton, 23, has a 3.07 ERA this season, and he’s led the Cubs to wins in four consecutive starts and 11 of his 16 outings in the 2025 season. Meanwhile, Peralta has a 2.90 ERA and has led Milwaukee to a win in 16 of his 25 outings in 2025. 

This is a pretty even matchup overall, but the Brewers are coming off a 14-game winning streak that was snapped on Sunday. Not only is Milwaukee firing on all cylinders, but it is one of the better road teams in MLB this season, moving to 11 games over .500 at 36-25. 

Chicago is very likely to be a playoff team, but I’m not totally sold on it winning this matchup – or betting on it as a favorite against the hottest team in MLB. 

Horton’s advanced numbers are a reason to doubt the Cubbies, as he ranks in the 45th percentile in expected ERA (4.00) and the 48th percentile in expected batting average against (.248).

Those aren’t horrible numbers, but they pale in comparison to Peralta (3.53 xERA and .222 xBAA) this season.

I’ll back the Brew Crew with Peralta on the mound in Game 1. 

Baltimore Orioles Moneyline (+104) vs. Boston Red Sox

Lefty Trevor Rogers has been a revelation for the struggling Baltimore Orioles this season, as he’s posted a 1.43 ERA in 11 outings while leading the O’s to an 8-3 record.

He’ll take on the Boston Red Sox and Dustin May (4.67 ERA) on Monday, as May attempts to build on a strong outing (six innings, five hits, no runs) in his last start against Houston. 

While May did turn things around in his second outing for Boston, he’s struggled a bit overall this season, posting a 1.35 WHIP and an expected ERA of 4.71, which ranks in the 19th percentile amongst MLB pitchers.

Boston has also slipped a bit as of late, winning just four of its last 10 games.

Baltimore is far from a playoff team, but it has rallied behind Rogers in the 2025 season. The lefty has an expected ERA of 3.05 (85th percentile), and he’s allowed three or fewer earned runs in every outing in 2025. 

I wouldn’t be shocked if he outduels May and leads the O’s to an upset win on Monday night. 

Toronto Blue Jays-Pittsburgh Pirates UNDER 7 (-107)

Paul Skenes is on the mound for the Pittsburgh Pirates on Monday, Aug. 18, and he’ll look to rebound from a rough outing against the Brewers his last time out.

Skenes allowed four runs in four innings in that matchup, just the third time in 25 starts that he allowed more than three earned runs in 2025. 

That leads me to tonight’s bet, as I’m leaning with the UNDER in this matchup with the Toronto Blue Jays.

Toronto is one of the best OVER teams in MLB this season, hitting it at a 57.5 percent clip, but the Pirates are one of the best UNDER teams, hitting it at a 57.0 percent clip. 

Pittsburgh ranks dead last in MLB in runs scored in 2025, and if there is ever a time to expect the Pirates’ pitching staff to keep an opponent in check, it’s when Skenes is on the mound.

So far this season, Pittsburgh has combined for seven or fewer runs in 16 of Skenes’ 25 outings.

On the Blue Jays side, Kevin Gausman (3.79 ERA) has pitched really well as of late, posting a 2.96 ERA in eight starts since July 1. He should keep this struggling Pirates offense in check on Monday night.

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Odds refresh periodically and are subject to change.

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