Top MLB Betting Picks for Monday, September 20th (2021)

The second-to-last Monday of the MLB regular season has a slate of 12 games. The Milwaukee Brewers became the third National League team to clinch a playoff spot over the weekend, while we are still waiting for the American League playoff picture to sort itself out.

Last week was another profitable week for our daily picks column, and we begin today with our highest bankroll (+17.53 units) of the season. Let’s continue our climb in the last two weeks of the regular season, with our goal of ending the week north of +20 units.

Today, our two picks involve a moneyline wager on an underdog and a contrarian play on a team total involving a hot offense.

Here are my MLB top betting plays for Monday. (Odds courtesy DraftKings Sportsbook)

View the best player prop bets for today’s slate with our MLB Prop Bet Cheat Sheet >>

YTD: 170-137-8 (+17.53 units) 

Pittsburgh Pirates ML (+155)

The Pittsburgh Pirates might be one of four teams in baseball with more than 90 losses at the moment, but they are not exactly limping to the finish line. The Pirates have won eight of their last 12 games and four consecutive series, including taking two of three from the Cincinnati Reds last week. Tonight’s starter, Dillon Peters, earned one of those two wins against the Reds, and we like him to duplicate that effort again on the road in tonight’s series opener. 

Peters (1-2, 2.66) is making his sixth start of the season, and he has racked up 20 strikeouts in 23.2 innings. He has pitched to a 2.84 ERA and a 1.16 WHIP over the last month, and Pittsburgh has to like what it has seen from their young lefty. In his last win against the Reds, Peters threw five scoreless innings and struck out five batters while limiting Cincinnati to five hits. Meanwhile, the Pirates face Cincinnati’s Vladimir Gutierrez (9-6, 4.25), who they roughed up for four runs in 3.2 innings in last week’s series. The Reds are 0-4 in Gutierrez’s previous four starts against teams with a losing record, and he has not won a home start since August 22. 

Even though Cincinnati is 16-5 in their last 21 home games against Pittsburgh, we love how the Pirates are playing lately, especially having won their last four series openers.

Philadelphia Phillies Team Total UNDER 4.5 runs (+105)

The Philadelphia Phillies had their four-game winning streak snapped last night, but they had their offense largely to thank for those wins. They scored at least four runs in every game in that span and averaged eight runs per game. However, they were foiled by lefty Rich Hill and face another lefty tonight. This year, the Phillies have not fared as well against lefties, ranking outside the top ten in both batting average and OPS against left-handed starting pitchers.

Baltimore sends lefty John Means (5-7, 3.41) to the mound, who has pitched much better over the last month. Means missed six weeks of action from early June to late July and did not look like himself in his first couple of starts back from injury. He allowed at least four earned runs in four of his first six starts post-injury but has allowed three earned runs or fewer in his last five starts and just two earned runs in each of his previous four. Means is susceptible to the long ball, having allowed a home run in four of his last five starts, but has allowed more than one home run just twice in his previous ten. Nevertheless, he should be able to neutralize Philadelphia’s biggest left-handed bats like Bryce Harper, Didi Gregorious, and Brad Miller, who have been responsible for much of Philadelphia’s offense of late.

The under is 5-2-1 in the last eight meetings between these teams and is 5-0 in Baltimore’s last five road games when they face a left-handed starter. Thus, we like for these two trends to help support Philadelphia’s case to struggle scoring runs tonight.

Subscribe: Apple Podcasts | Spotify | Google Podcasts | Stitcher | RadioPublic | Breaker | Castbox | Pocket Casts

Whether you're new to sports betting or a betting pro, our Sports Betting Strategy and Advice page is for you. You can get started with our 101 section - including 10 Sports Betting Tips for Beginners - or head to more advanced strategy - like Key Numbers When Betting Against the Spread - to learn more.

Mike Spector is a featured writer at BettingPros. For more from Mike, check out his archive and follow him @MikeSpector01.