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MLB Best Bets Today: Top underdog picks for Monday 7/20/26

MLB Best Bets Today: Top underdog picks for Monday 7/20/26

Published:

By: Zach Thompson

Who doesn’t love an underdog?

Betting on an underdog is the easiest way to get the most bang for your buck with a single wager, yet it’s always a somewhat risky endeavor. I mean, they’re underdogs for a reason, right? Still, there’s no sport where the underdog comes through more often than in baseball. It’s a 162-game season. Even the best teams are going to lose about 60 times a year.

With that in mind, let’s go looking for dogs this Monday night on the DraftKings Sportsbook.

Best MLB Underdog Bets, Picks

Padres ML (+109)

Monday’s slate features several games that are extremely close on the Moneyline, and in one of the interesting and even matchups, the Padres are slight plus-money underdogs for the start of their series with the Braves in Atlanta. JP Sears will start for the Friars against Bryce Elder of the Braves. The Braves are about eight games better in the standings, but the Padres were able to avoid a sweep with a big 19-2 win over the Royals on Sunday, while the Braves started the second half by taking two of three games from the Rangers in a high-scoring home series in Atlanta.

The Braves are hard to pick against at home, but Elder is 5-6 with a 4.12 ERA overall this season and has allowed at least four runs in four straight starts, allowing 23 runs on 32 hits in just 18 innings. Elder will face a Padres lineup that seemed to get going on Sunday and will hope to carry over that momentum from its 19-run outburst.

On the other side of the matchup, the Padres have been getting solid outings from lefty JP Sears, whose overall numbers are not outstanding, but most of that is due to one brutal outing. He held the Braves to just two runs in 5 2/3 innings when he faced them on June 24, in a game the Padres won, 5-2. With how much Elder has struggled and Sears’ solid start against Atlanta earlier this year, the Padres have a chance to pull off the upset this Monday night to start the series.

Tigers ML (-105)

In another coin-flip matchup, the Tigers are very slight underdogs at -105 as they visit the Cubs at Wrigley Field, but I like them to open the series at Wrigley with a win behind Jack Flaherty. I highlighted Flaherty in my top value plays for the day, and he has looked very sharp since returning from the IL. He’s allowed just two runs in 16 2/3 innings over those three starts. He got wins in his last two outings against the Phillies and on the road against the Rangers.

Both teams won two of three games in their first series after the All-Star break, with the Cubs taking two games from the Twins and the Tigers defeating the Angels twice. This is the first game of their only series of the year, but Flaherty gives the Tigers a big advantage over Jameson Taillon, who starts for the Cubs after missing a month with a hamstring injury. Before the injury, Taillon had struggled to a 2-5 record with a 5.19 ERA and 1.30 WHIP, allowing 20 homers in his 13 starts.

The Tigers are trying to climb back into the playoff race enough to be able to keep Tarik Skubal and make a push to October, and they are 9-4 in July. The Cubs are also in the playoff push, but they are 8-5 this month with a little less momentum. Even though both teams need another big series, the Tigers have the advantage thanks to Flaherty and have a good chance to take the first game of this set.

Cardinals ML (-108)

We’ll go out west to find the third play in our MLB underdog picks this Monday. The Cardinals are facing the Angels in the latest game on the schedule, and they’re very slight road underdogs. The Cardinals lost two of three in Arizona after the break, losing Sunday to a late Arizona rally in extra innings. They have faded a bit after their hot early start, but they’re still clinging to the third and final NL Wild Card spot at 51-47. The Angels are at the bottom of the standings in the American League with a 39-61 record that is the worst in the MLB. The did manage to avoid a sweep to start the second half by beating the Tigers, 3-2, on Sunday night.

The Cardinals will give the ball to Kyle Leahy to start their series in Anaheim, and he’ll take on Jose Soriano. Both pitchers have had very solid seasons, but Soriano got a lot more attention for his early dominance, which may be a big part of the reason the Halos are slight favorites. After beginning the season hot, though, Soriano is 2-4 with a 5.24 ERA and 4.76 FIP in his last 11 starts. Leahy has only allowed one run total in his last four starts (spanning 19 1/3 innings), and he has a 2.96 ERA and 3.25 FIP over his last 11 starts.

The Cardinals’ lineup has more exciting young pieces in place, and the team as a whole is headed in a better direction. With an advantage at starting pitcher as well, this is a great spot to round out Monday’s underdog picks. I also included this matchup as one of my top NRFI plays earlier today if you’re looking for a quick hit that won’t take until the end of the game to settle.

I am a promoter at DraftKings and am also an avid fan and user (my username is z.thompson) and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skills and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.