Monday’s Major League Baseball schedule features intense battles as the Milwaukee Brewers face the Chicago Cubs in a pivotal doubleheader, while the Baltimore Orioles prepare to take on the Boston Red Sox. Meanwhile, Paul Skenes looks to bounce back on the mound for the Pittsburgh Pirates against the Toronto Blue Jays. These contests capture the urgency of teams competing for playoff positioning and highlight key pitching matchups that could shape the season’s final stretch.

Tuesday’s Crucial MLB Games Spotlight Tight Races and Key Pitchers

The Brewers and Cubs, two top teams in the National League Central division, open Monday’s action with a doubleheader aimed at securing stronger playoff positioning. Milwaukee holds the best record in MLB this year and has would like to extend its momentum following a recent fourteen-game winning streak that was snapped. Chicago follows closely, leading the NL wild card race as a firm playoff contender. Both squads understand the stakes as the season winds down, with wins being essential to lock in postseason spots.

The Orioles continue their surprising surge in the American League East, chasing wins behind effective pitching from Trevor Rogers. Rogers’ performances have been standout in 2025, giving Baltimore hope despite the team’s broader struggles. On the other side, the Boston Red Sox try to stabilize after a shaky recent stretch that saw mixed results and inconsistent pitching, notably from Dustin May. This matchup has the potential to spring an upset, with Rogers’ recent dominance contrasting against May’s uneven form.

Meanwhile, the Pittsburgh Pirates, led by Paul Skenes on the mound, aim to capitalize on home-field advantage against the Blue Jays. Skenes, despite a difficult outing against Milwaukee recently, has demonstrated strong potential throughout the season and hopes to reassert his influence. Toronto’s offense is one of MLB’s most prolific, making this an intriguing duel between a high-powered lineup and a developing pitching staff.

Detailed MLB Best Bets for August 18

According to DraftKings Sportsbook odds, three primary bets stand out for Monday’s games:

• Milwaukee Brewers Moneyline at +108 against Chicago Cubs
• Baltimore Orioles Moneyline at +104 versus Boston Red Sox
• Under 7 runs for the Toronto Blue Jays and Pittsburgh Pirates game at -107

Milwaukee Brewers Favored Over Chicago Cubs in First Game

Game 1 of the Brewers-Cubs doubleheader features a compelling pitching head-to-head between Milwaukee’s Freddy Peralta and Chicago’s Cade Horton. Peralta, Milwaukee’s ace, carries an impressive 2.90 ERA in 2025, contributing significantly to the team’s outstanding win record. His consistency makes Milwaukee a formidable opponent, particularly on the road where they have an 11-game winning margin over .500.

Horton, a rising talent, has also performed well, boasting a 3.07 ERA and leading the Cubs to victory in the majority of his starts this season. However, his advanced metrics suggest some vulnerabilities; his expected ERA and batting average against rank only near the mid-point of MLB pitchers, contrasting with Peralta’s stronger expected performance indicators.

Despite Chicago’s status as one of the likely playoff teams, Milwaukee’s momentum and pitching advantage position the Brewers as the favored team in this matchup. As the hottest team this season, backing Peralta’s Brewers in the opening game appears to be a solid prediction.

Baltimore Orioles Aim for Upset Against Boston Red Sox

Trevor Rogers has been a bright spot for Baltimore, posting an outstanding 1.43 ERA in his 11 outings this season and leading the team to an 8-3 record during his starts. His efficient control and consistent performance at the mound have fueled Orioles’ optimism, despite the team still trailing playoff contention overall.

The opposing pitcher, Dustin May, has struggled at times this year, showing a 4.67 ERA with underlying metrics that place him in the 19th percentile of MLB pitchers, signaling inconsistency and room for improvement. Boston’s recent form also reveals some decline, with only four wins in their last ten games.

Given these factors, Rogers’ steady dominance and May’s uneven results raise the possibility of Baltimore pulling off an upset on Monday night. The matchup emphasizes the contrast between a rising Orioles pitching staff and a Red Sox rotation still finding its footing.

Low-Scoring Expectation in Toronto Blue Jays vs. Pittsburgh Pirates Game

Pitcher Paul Skenes takes the mound for Pittsburgh, seeking to recover from a challenging outing in which he allowed four runs over four innings against the Brewers. Such setbacks have been rare in an otherwise solid season of 25 starts. His ability to manage opposing offenses will be tested against a strong Blue Jays team known for their offensive firepower.

While Toronto ranks near the top with 57.5 percent of its games going over the total runs line, Pittsburgh’s games tend to lean under, also at roughly a 57 percent rate. The Pirates collectively score the fewest runs in MLB in 2025, emphasizing their reliance on limiting opposition scoring to compete.

Going into this contest, 16 of Skenes’ 25 starts have resulted in seven or fewer combined runs, reinforcing confidence in a low-scoring outcome. Blue Jays pitcher Kevin Gausman, with a recent ERA below 3.00, also projects as a strong counterbalance against the Pirates’ offense. This data supports placing a bet on the under in this matchup.

The Broader Significance of These Contests and Paul Skenes’ Role

The upcoming games highlight critical junctures for several MLB teams pursuing playoff berths, with pitching quality playing a vital role in determining outcomes. Milwaukee’s efforts to maintain its league-best record, Baltimore’s search for momentum, and Chicago’s drive for a wild card spot all converge as pressure mounts.

Meanwhile, Paul Skenes represents one of Pittsburgh’s hopes to stabilize and improve their pitching staff’s reputation. His MLB pitching prediction for this game reflects optimism for a strong rebound, which could have lasting impact on how the Pirates perform down the stretch. The success of these matchups will influence the playoff landscape, intensifying the race as teams position themselves for the postseason.