Time to start the week off right with the MLB Best Bets and Prop Bets for today, Monday, May 20. The action on Monday starts early with the first game of a doubleheader between the San Diego Padres and Atlanta Braves beginning at 12:20pm ET and then continues with a 3pm ET start between the Chicago White Sox and Toronto Blue Jays




We will likely leave the Padres vs. Braves game alone for MLB betting as lineups haven’t been released as of writing this and we all know how managers move players in and out for doubleheaders. The rest of the games are all very much in-play and we’ve got some great matchups to break down for today’s MLB predictions.

MLB Picks, Predictions, & Best Bets Today, 5/20

We finished last week with a strong day of betting on Friday and our bankroll is looking really good a month and a half into the 2024 MLB season! 

We don’t want to get too far ahead of ourselves just yet, but once we officially clear the 20-unit threshold, we can get a little more aggressive with Same Game Parlays and other creative bets to get us some better odds. For now, we maintain the process that has been working for us so far. 

  • Friday’s Record: 6-2-1
  • Season Record: 140-108-4
  • Bankroll: +19.82 units

*Each of my MLB picks will have accompanying odds listed next to them.




White Sox vs. Blue Jays Prediction: Monday, May 20

Two of the less-inspiring teams square off today with an interesting pitching match-up. On the Jays side, you have Jose Berrios who has been absolutely fantastic this season with a 2.82 ERA and 1.05 WHIP. We watched him regain form last season and save for one poor outing against a hot Phillies lineup, the righthander has been solid. Can he maintain against a soft White Sox lineup? I believe he will. 

On the other side, Erick Fedde takes the mound and he’s been on-fire lately, tossing 13 straight innings without allowing a single run. He also has nine strikeouts with no walks in that span. Now he’ll face a Blue Jays lineup that has been incredibly disappointing all season. 

In fact, the Jays have the fifth-lowest wOBA (.297) with a 20.3-percent strikeout rate against righties this season and have just a .275 wOBA with a feeble .117 ISO over the past week. If they continue down this path, Fedde should be able to contain the lineup for the first few turns through the order.




Angels vs. Astros Prediction: Monday, May 20

The Astros have been one of the hottest hitting teams in MLB over the past week, posting an impressive .363 wOBA with a .198 ISO. They’ve also been fantastic against southpaws this season with a .342 wOBA and a strikeout rate that lives below 17-percent. We'll look to target their lineup in the next of today's MLB predictions.

Angels lefty Reid Detmers has pitched into the sixth inning just once in his last six starts and has allowed 27 earned runs over that span (33 innings) with seven home runs allowed. I expect the Astros to jump on him early, work that pitch count up and chase him. The books originally had him at 17.5 outs for his prop late last night but changed it immediately. We can get him here at 16.5 and still feel good about it.




Brewers vs. Marlins Prediction: Monday, May 20 

A bit of a soft matchup here pitching-wise, which leads me to a lot of runs being scored, despite the fact that the Marlins have been a weak lineup throughout the season. However, they’ve been seeing the ball a little better lately and averaged seven runs per game during this recent homestand. Joe Ross pitches to contact and his barrel rate against him has spiked to just over 10-percent. If the Fish continue to make contact, they should put some runs up on the board.

The Brewers remain one of the hottest-hitting lineups in MLB right now with a .357 wOBA and .192 ISO over the last seven days. That includes a .317 wOBA against southpaws this season. They’ll be squaring off against lefty Ryan Weathers who also pitches to a lot of contact. He’s been a solid starter with three-straight quality starts, but the luck runs out against this Brewers lineup. 

And just to add to the reasoning behind the bets, both bullpens have been overworked over this past week and neither has performed at a level to believe they will keep the runs off the board even after the starters are gone.




Best MLB Props For Today, 5/20: Strikeout Bets