DraftKings Daily Fantasy Baseball Picks (5/20/21): MLB DFS Lineups

The top daily fantasy baseball lineup picks for DraftKings on 5/20/21. Brian Entrekin's MLB DFS analysis and sleepers for building optimal DFS rosters.

We have a 4-game early and 4-game main slate on tap tonight, and they are some rough slates. This article will focus on the main slate as usual, but you can listen to MLB DFS Quick Hits to get a breakdown for both of today's slates. Pitching is overall bad tonight, and the hitting spots are going to be quite popular. When playing a four-game slate, being contrarian feels extra dirty but is the only way to win it all.

The slate starts with the ugly pitching decision. Outside of Alcantara and Smyly (discussed below), there can be arguments for Merrill Kelly and Vincent Velasquez. My goodness, this doesn't sound very good. When it comes to the bats, the focus will be on Coors South between the Red Sox and the Jays. The funny part is two of the three most expensive pitchers tonight pitch in Dunedin, but the environment and the quality of bats lead me to a full game stack. Outside of Dunedin, there are a few other spots to differentiate if needed. The bottom line, the evening slate is nasty, and everyone should tread lightly.

This article will provide you with my daily fantasy baseball lineup picks for DraftKings on 5/20/2021. The lineup will range from some of the elite players to mid-priced options and value plays. You can also check out today's FanDuel MLB DFS lineup picks and read more DFS advice and lineup picks for other sports too. It’s also important to monitor injury news and today's MLB starting lineups. If you have any questions or comments, contact me on Twitter @bdentrek.

DraftKings DFS Starting Pitchers

Sandy Alcantara - P, MIA at PHI ($9,300)

Alcantara was having a great season until his last start in Los Angeles, where the Dodgers scored eight runs and chased him from the game after 1.1 innings. Alcantara was coming off of three great starts where he threw at least six innings, allowing no more than two runs and striking out six in each of his last two starts. Alcantara brings his 24% strikeout rate, amazing 2.8% barrel rate, 39.7% hard-hit rate, and strong 48.2% groundball rate into tonight's action versus the Phillies. The Phillies offense has quieted down a bit of late and is battling a handful of injuries. On the season, they are striking out 26% of the time versus RHP with a .236 average and 91 wRC+. J.T. Realmuto may miss another game, and Didi Gregorius is on the IL. On a slate with a lot of questionable pitching, Alcantara checks the box as my top pitcher tonight.

Drew Smyly - P, ATL vs. PIT ($8,400)

Those that listen to Quick Hits know just how much I love fading Smyly. Well, here we are with Smyly as my SP2. The slate is really bad, resulting in the use of Smyly, plus he has been quite strong his last two starts and gets the Pirates tonight. Smyly has thrown six innings in each of his last two starts while allowing one run in each start and striking out four. Still, be a bit wary as his 0.75 ERA over the two starts still has a 5.17 xFIP. Smyly maybe who we always thought he was, but for tonight we roll. He takes on a Pirates team struggles versus LHP. On the season, the Pirates are striking out 24% of the time versus LHP with a .210 average, a .124 ISO, and a measly 78 wRC+. We roll with Smyly tonight and hope he has one more good start in him against a Pirates team he should fare well against.

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DraftKings DFS Infielders

William Contreras - C, ATL vs Wil Crowe ($3,700)

Contreras has run away with the Braves' starting job after injuries forced the Braves to bring Contreras up before they likely wanted to this season. Over the last seven games, Contreras is hitting .333 with hits in five of seven games. He is flexing his muscle with a crazy good .444 ISO and 1.278 OPS. The young Contreras is even showing great plate discipline by walking 16.7% of the time. He is doing a little bit of everything, has continued to stay affordable, and now gets a great matchup versus Crowe tonight. So far this season, Crowe is allowing RHH to hit .289 and a .378 SLG. The Braves make a great pivot off the popular game in Dunedin, with Contreras being a nice piece of that Braves stack.

Bobby Dalbec - 1B, BOS at Steven Matz ($3,000)

Bobby D is slowly getting things going for the Red Sox. Over the last 10 games, he has hit safely in seven games for a .294 average. He has even hit three home runs over the last 10 games with a .382 ISO and 177 wRC+. He is absolutely raking, backed up by a 25% barrel rate and 41.7% hard-hit rate. Dalbec will look to carry the hot streak into tonight's home run derby versus Matz. Matz started the season strong but has allowed three or more runs in four of his last five starts, as well as allowing five home runs over that stretch. Four starts ago, he faced the Nats in Dunedin and allowed six runs over 3.2 innings. Look for the Sox to be popular tonight, but likely popular for a perfect reason. Making Dalbec a nice value Red Sox piece tonight.

Kike Hernández - 2B/OF, BOS at Steven Matz ($3,400)

Hernández missed some time with an injury but returned two days ago and picked up where he left off. He has hit safely in both games since returning and has a 6-game hitting streak overall. He absolutely smashed last night, going 3-5 with a double and a home run, good for 24 DK points. He will likely be leading off again tonight for the Red Sox, which bodes well for his value as he loves facing LHP. It is also nice that Matz has been hit hard by RHH; some may say the perfect storm. On the season, RHH is hitting .250 versus Matz and a .425 SLG. Hernández will be extremely popular tonight, as he should be, and should still be used in cash games as well as Red Sox stacks.

Jazz Chisholm - 2B/SS, MIA at Vincent Velasquez ($4,400)

Let's keep getting Jazzy with it, especially at a discounted price compared to his talent level. Chisholm missed a few weeks with a hamstring injury but returned three games ago and has picked up where he left off. He has hit safely in all three games with a home run and even a stolen base. He has scored five, 13, and 21 DK points in those three games, showing great production for cash games and tournaments. Tonight he is even more in play as most will play the main 2B and SS featured in Dunedin, leaving Chisholm lower rostered in a terrific matchup versus Vinny V. In his career, Velasquez has allowed LHH to hit .270 with a .468 SLG and close to 1.5 HR/9. The Marlins are a nice, sneaky stack tonight, led by Jazzy Jazz Chisholm.

Austin Riley - 3B, ATL vs. Wil Crowe  ($3,500)

Riley is absolutely raking these days, and DK continues to misprice him. Riley has hit safely in four straight games, hitting .500 with two doubles and two home runs. He is hitting everything well with a 50% barrel rate and 75% hard-hit rate over the four games but has also shown great plate discipline by walking 18.8% of the time. Riley has scored 14 or more DK points in each game and now gets an awesome matchup versus Crowe tonight. Riley is far too cheap for his matchup and for the way he is swinging the bat, so enjoy some hopefully low-owned Riley tonight.

DraftKings DFS Outfielders

Alex Verdugo - OF, BOS at Steven Matz ($3,800)

The Red Sox will be super popular tonight, which makes sense, but a way to be a bit different is rostering Verdugo versus an LHP as he hits them quite well. Most will look for all the RHH mashers, making sense, but do not sleep on Verdugo. Over the last two seasons, he has hit over .300 in both seasons versus LHP, and this season is hitting .271 versus lefties. The last two seasons even saw Verdugo put up a 117 and 121 wRC+ versus LHP, but this season is down just a bit to 86. Verdugo is swinging a hot bat as well, with multi-hit games in three straight starts, including two home runs and a double. Do not sleep on Verdugo tonight just because it is a lefty versus lefty situation.

Teoscar Hernandez - OF, TOR vs Nick Pivetta ($4,700)

Sure Marcus Semien, Bo Bichette, and Vladimir Guerrero Jr are all hitting well, do not sleep on Teoscar. Teoscar has hit safely in eight of his last nine games, good for a .471 average. He has five XBH and a stolen base to go with a .265 ISO and 1.273 OPS. Yeah, that is not a typo, as Teoscar has a .538 OBP over the last nine games, thanks to a 12.8% walk rate. He's putting the ball in play a ton and walking a lot as well, but the most impressive stat over the last nine games may be the fact he is striking out a measly 10.3% of the time. Teoscar is absolutely locked in right now and has been my third piece of Jays' stacks nightly behind Semien and Bichette. Please do not sleep on Teoscar tonight as he will find the bleachers in Dunedin.

Adam Duvall - OF, ATL at Vincent Velasquez ($3,900)

Let's pick on Vinny V a bit more tonight. Insert Duvall has been heating up of late, hitting safely in five of his last six games. Over the six games, he is hitting .348 with a .261 ISO and 155 wRC+. Duvall has hit two home runs over the last six games while barreling the ball 10.5% of the time. Most think Duvall is just a lefty masher, but do not sleep on the fact he has a .192 ISO and .242 average versus RHP this season. More importantly, is the fact he is facing Vinny V tonight, who has given up a lot of power to RHH this season. RHH is slugging .500 versus Vinny V while hitting 3 HR/9 this season. Duvall will be virtually non-rostered tonight and makes for a great GPP one-off as well as a piece of the Marlins stack.

DraftKings DFS Stacks

• Boston Red Sox (Steven Matz, LHP)
• Toronto Blue Jays (Nick Pivetta, RHP)
• Atlanta Braves (Will Crowe, RHP)
• Sneaky Stack-  Miami Marlins (Vincent Velasquez, RHP)