MLB Prop Bets, Picks and Predictions for May 20

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Updated: May 20, 2021

Vladimir Guerrero Jr. is hitting .327 with 11 home runs and 31 RBIs, and his 1.053 OPS trails only Mike Trout this season.

Photo By – USA TODAY Sports

It’s another getaway day on the MLB schedule, which means one thing. All-day MLB prop betting! And today is highlighted by two of the Big League’s hottest hitters.

We start this afternoon in Cincinnati where Jesse Winker looks to continue a red-hot start against the San Francisco Giants, and then we turn our attention to Dunedin where Blue Jays phenom Vladimir Guerrero Jr. is tearing the cover off the ball.  

We break down and pick those games and more with our best free MLB prop bets and predictions for Thursday, May 20. 

Today’s MLB props and picks

Jesse Winker Over 1.5 Total Bases (-110)

Cincinnati Reds outfielder Jesse Winker has cooled off a bit after his red-hot start. Of course, cooled-off is a relative term here. Winker has gone from hitting a ridiculous .375 to just an awesome .343, which includes 4-12 (.333) this series against the San Francisco Giants. 

The Reds slugger has quietly been one of the best hitters in baseball this season and sports a .999 OPS. Winker also has 16 multi-hit games and 19 extra-base hits this season, and now gets to go up against the Giants’ Johnny Cueto.

The right-hander has looked rusty in his two starts since coming off the IL for a lat strain, having surrendered 16 hits in just 7 1-3 innings of work. That makes Winker a good value to go over his total bases prop in this one.

Covers MLB betting analysis

Marlins-Phillies Under 4.5 Five-Inning Total (-125)

The Miami Marlins and Philadelphia Phillies play the rubber match of their three-game series Thursday night at Citizen’s Bank Ball Park. The Phillies took the opener 8-3 while the Fish responded in Game 2 with a 3-1 victory, and the finale has all the makings of a pitcher’s duel.

Miami hands the ball to Sandy Alcantara, and while he is coming off one of the worst starts of his career, don’t be surprised if the right-hander bounces back quickly. Prior to getting torched by the Dodgers for eight runs on seven hits in just an inning and a third, Alcantara had pitched to a 2.72 ERA and was limiting opponents to a .203 batting average.

Alcantara now faces a Phillies lineup that while talented, certainly seems all-or-nothing. For example, in their last six games, they have scored five or more three times and one or fewer three times.

Countering Alcantara is Vince Velasquez, who has looked rejuvenated since rejoining the Phillies’ rotation at the end of April. The right-hander has pitched to a 2.84 ERA and is limiting opponents to a .200 average in five starts since April 23.

He goes up against a Fish team that is floundering at the dish, ranking 25th in scoring and 26th in OPS. Bet on pitching to be the story early on in this one.

Vladimir Guerrero Jr. Over 1.5 Total Bases (+105)

Remember when Vladimir Guerreo Jr. was a bust? Yeah, me neither. The Toronto Blue Jays first baseman is tearing the cover off the ball, still just a 22-year-old. Guerrero is hitting .327 with 11 home runs and 31 RBIs, and Vladdy’s 1.053 OPS trails only Mike Trout this season.

Guerrero is currently on a six-game hitting streak where he is 10-25 (.400) with six extra-base hits and has only struck out once. Thursday, he and the Jays go for the series win over the division-leading Boston Red Sox.

Boston puts its best foot forward by handing the ball to right-hander Nick Pivetta. Pivetta has been the BoSox’s best starter this season and over his last five starts, he is pitching to 2.89 ERA and is limiting opponents to a .158 batting average.

So, does that mean a tough day for Vladdy? Well, the advanced stats aren’t as kind to Pivetta. When he is getting hit, he is getting hit hard and he doesn’t get hitters to chase a lot of pitches, which is Guerrero’s specialty. 

Look for Vladdy to be patient in this one and clobber a Pivetta pitch that catches too much of the plate. 

Yesterday’s MLB record: 2-1, 0.58 units
Season MLB betting record: 69-74-3, -7.5 units

MLB betting card for May 20

  • Jesse Winker Over 1.5 Total Bases (-110)
  • MIA-PHI Under 4.5 Five-Inning Total (-125)
  • Vladimir Guerrero Jr. Over 1.5 Total Bases (+105)

Picks made on 5/20/2021 at 11:20 a.m. ET

MLB parlays

Did you know that if you parlayed today’s MLB prop picks, you could win $60.45 on a $10 bet?

Use our MLB parlay calculator to create your own parlays and see their potential payouts.

Where can I bet on MLB props?

You can bet on MLB props at every online and casino sportsbook, including MLB player props, derivatives, and a ton of other MLB prop odds. Head over to our best-suggested sportsbooks for the top spots to bet on MLB props in your area.


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