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MLB Best Bets: Top Starting Pitcher Prop Bets for Monday ...
Zach Thompso · 2026-05-19 · via DraftKings Network

Zach Thompson details his top starting pitcher props for Monday’s MLB slate on DraftKings Sportsbook.

Only two Major League Baseball teams have Monday off, with some great matchups on the board to start the week off with some exciting matchups. While there are plenty of fun home run props and DFS fantasy baseball contests on the board, it’s also a great night to explore some of the many options offered for starting pitcher prop bets on DraftKings Sportsbook. In this post, you can find my top plays for Phillies SP Andrew Painter, Yankees SP Ryan Weathers and Rangers SP MacKenzie Gore.

In almost every MLB contest, starting pitching is key to deciding how the matchup will play out. DraftKings Sportsbook offers plenty of different varieties of SP prop bets, so let’s survey the field and find some fun ones to target this Monday night.

Top MLB SP Props

Andrew Painter to Record a Win (+247)

Let’s start with a long-shot play from Philly, where the Phillies host the Reds to start the week. The wind is blowing out and the temperatures will be warm, so there could be plenty of offense in this matchup. However, I like the Phillies’ chances to deliver more offense against Nick Lodolo. Lodolo has an 8.68 ERA and 7.49 FIP, giving up four runs in 5 1/3 innings to the Astros and five runs in four innings in his last start against the Nationals.

Painter has had his own ups and downs but the big 23-year-old righty still has the potential to develop into an ace. He is 1-4 with a 6.21 ERA, but his 4.28 FIP and .350 BABIP against him indicate he has been very unlucky with batted-ball luck.

He has gone at least five innings in three of his last four starts and gave up three runs or fewer in four of his last six. He only gave up one run on four hits in five innings in Fenway Park in his last outing but was stuck with a no-decision.

The Phillies are surging, having won seven of their last eight coming into this series and winning their last two games by identical scores of 6-0 over the Pirates. The Reds are trending the other way, going just 4-12 in their last 16 games and losing four of their last six. Cincinnati’s offense didn’t get much going against the Guardians, losing two of three in its in-state rivalry over the weekend.

With Lodolo struggling and the Phillies heating up, I see this as a great spot for Painter to get a win and bring great value at these longshot pitcher prop odds this Monday night.

Ryan Weathers o17.5 Outs Recorded (-108)

Weathers and the Yankees host the Blue Jays in the Bronx to start the week, and Weathers will look to continue his recent run of strong results. He will need to get through six full innings to deliver the win at this SP prop for this Monday, but with the Jays in town, he has a good shot to get there.

Weathers recorded 19 outs in his most recent start in a no-hit bid that ended in the seventh inning. He went over this prop in three of his last six starts. He went eight strong in a loss to the Athletics in his best home start of the season. He’s averaging 17.4 outs per home start on the season, but since he has been so strong lately, I like his odds to get at least six innings on Monday.

Toronto is hitting only .222 against lefties this season with a .299 wOBA. Over the last two weeks, it has scored just 45 runs in 12 games for the seventh-lowest mark in the majors and is hitting only .216 as a team.

Weathers has a good chance to keep the Jays slumping on Monday and should get through at least six frames.

MacKenzie Gore o5.5 Strikeouts Thrown (-150)

Yup! We’re taking a starting pitcher prop at Coors Field–look out world!

Gore has gone 3-3 in his nine starts for the Rangers with a 4.50 ERA and 3.95 FIP. He has 53 strikeouts in his 48 innings, racking up at least five punchouts in seven of his nine outings. He had five strikeouts in his longest start of the season in his last start against the Diamondbacks, working eight innings and allowing just one run on three hits.

He did come in under this prop line in that excellent start, though, so why is the over a strong play? The Rockies strike out at one of the highest rates in the MLB. Against lefties, they lead the league with a 29.8% K%.

The weather will also be helping Gore a little bit with very cold temperatures and the wind blowing in. Coors Field can always be tough, but the environment should actually help him have a good start in this matchup. He’s a solid play to get the win and go deep in the game, but of all his starting pitcher props available, his strikeout prop is my favorite play since he can be so dominant at his best.