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Best MLB Bets Weekend | MLB Picks, May 20-21

Written by: Michael Hanich
Published May 20, 2023
13 min read
MLB Picks, May 20 - 21

All 30 MLB teams enter the final days of May as the 2023 MLB Season is going fast for players, personnel and fans. 

Now is the time for teams to start developing good habits and show why they are serious contenders for the postseason. This weekend's slate of games are going to be affected by most of the injuries of the league's biggest stars. Among the major injuries to watch for from now until the All-Star Break are the Tampa Bay Rays' bullpen and a San Diego Padres' star. 

While there are games that look easy to win earnings, looks can be misleading.

Milwaukee Brewers @ Tampa Bay Rays

Time: 4:10 PM E.T.

Odds courtesy of DraftKings Sportsbook

My Pick: Tampa Bay Rays (TB)

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One of the top afternoon games on Saturday will be set between the Tampa Bay Ray (33-13) hosting the Milwaukee Brewers (24-20), who are still an efficient team despite losing high-level talent. This game looks to be a one-sided matchup between the leaders of their respective divisions, but there is going to be more to this game than stats, which is something that bettors need to take note of.

The Rays are projected to start Zach Eflin (3.38 ERA in 40 innings pitched) on Saturday against the Brewers. While Elfin has been efficient through the majority of the season, he has given up the most hits at 38 and delivered 44 strikeouts. The biggest for the Rays is that two of their best pitchers on the team in Jeffrey Springs and Drew Rasmussen are currently on the 60-day IL.

Tampa Bay will face a Brewers' batting team that is currently ranked 11th in the NL in runs accounted for (183), 14th in hits accounted for (337), 13th in strikeouts encountered (397), 13th in batting average (.239) and 14th in on-base percentage (.316). The Brewers are a team that likes to rely on their power hitters to help get runs and set up scoring situations.

The caution sign for the Rays is their recent trend against teams with poor batting rhythm. In the previous series at the New York Mets, a team that is inconsistent at best at the plate, has defeated the Rays in two of the three games a few days ago. On Friday night, the Rays barely squeezed out a 1-0 win over the Brewers in the first game of the series.

It is smart to bet on the Rays due to their talent, but it might difficult for them to believe they will score the over.

Los Angeles Dodgers @ St. Louis Cardinals

Time: 7:15 PM E.T.

Odds courtesy of DraftKings Sportsbook

My Pick: Los Angeles Dodgers (LA)

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This Saturday is set to feature a matchup that would normally be perceived a blowout. The difference maker of Saturday's game is the projected starting between the Los Angeles Dodgers (29-17), one of the hottest teams in the MLB, and the St. Louis Cardinals (19-17), the team with the second-worst overall record in the NL.

On Saturday, the Cardinals will be starting Miles Mikolas (4.91 ERA in 47.2 innings pitched), who is just after ace pitcher Jordan Montgomery of the best-starting pitchers for the Cardinals this season. The Cardinals rank seventh in the NL in ERA (4.29), 15th (last) in hits allowed (412), 12th in runs allowed (212) and seventh in home runs allowed (51).

The Dodgers wil be starting Noah Syndergaard (5.94 ERA in 36.1 innings pitched), who is a rough start to the 2023 MLB Season. He has accounted for a win-loss record of 1-3 this season. Syndergaard starting for the Dodgers would usually give the Cardinals the edge, but still the difference in the batting game.

The biggest difference maker will be the efficiency of both teams at the batting team. The Dodgers rank first in the NL in runs accounted for (245), first in home runs accounted (74), first in walks (200) and fifth in on-base percentage (.325). The Dodgers are an offensive juggernaut as they have six players who have accounted for more than 20 runs this season.

While the Cardinals have some talented batters, they are not to the production level of the Dodgers. Even with the pitching disadvantage, the Dodgers are very likely to take Saturday’s game.

Boston Red Sox @ San Diego Padres

Time: 10:10 PM E.T.

Odds courtesy of DraftKings Sportsbook

My Pick: Boston Red Sox (BOS)

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The Boston Red Sox (24-20) have been up and down significantly in the month of May. They swept through the Toronto Blue Jays for games and then won two of eight games a series later. The San Diego Padres have been a disappointment through the first 44 games of the season.

On Saturday, the Red Sox will be starting ace Chris Sale (5.40 ERA in 43.1 innings pitched), who is the second-best starting pitcher statistically. The Red Sox have had a tough slate of pitching performances this season as they rank 12th in the AL in ERA (5.00), 13th in hits allowed (399), 12th in runs allowed (232) 13th in home runs allowed (61) and 11th in strikeouts accounted for (371). Sale has been among the starting pitchers that have held the bullpens together.

Sale will face off against the underwhelming batting team of the Padres. Through the first 44 games of the season, the Padres rank 14th in the NL in runs accounted for this season (172), 15thb (last) in hits accounted for (325), ninth in home runs (46), 12th in strikeouts encountered (393), 15th in batting (.226) and 12th in on-base percentage (.317).

To make matters worse for the Padres, star third baseman Manny Machado was put on IL due to a fractured left hand. It is going to be much to ask for a Padres team with no momentum to turn their luck around, especially without Machado. Expect the Red Sox to get a solid win and rise in a loaded AL East Division.

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Michael Hanich

498 Articles

Michael Hanich is a sports journalist/analyst with a wide variety of experience in the newspaper and digital field. He has a love for all sports. The leagues that he covers are College Football, the NFL, the NBA, the NHL, College Basketball (men’s and women’s), the MLB, Lacrosse, Volleyball, and the WNBA.

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