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MLB Best Bets Today: Top underdog picks for Monday 7/27/26

MLB Best Bets Today: Top underdog picks for Monday 7/27/26

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. Over the course of 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

Blue Jays Moneyline (+104)

Max Scherzer is the headliner here as he pitches for the Blue Jays in a return to his former stomping grounds in Washington, D.C. Scherzer hasn’t pitched in MLB since June 10, when he made his first start after missing all of May with an injury. He has been dealing with back spasms and a thumb injury all season and is an ugly 1-4 with a 10.23 ERA in his six starts. The 41-year-old righty threw five shutout innings in his rehab start in Triple-A Buffalo on Wednesday, and perhaps a return to Nationals Park can get him back on the right track.

He’ll be taking on Eddy Yean, who will open for the Nationals in front of Andrew Alvarez. Yean hasn’t allowed a run in 5.3 innings in MLB this year after posting a solid 3.35 ERA, 1.09 WHIP and 47 strikeouts in 43 innings out of the bullpen for Triple-A Rochester. Alvarez has struggled, though, allowing 3-plus runs in three straight outings, going 0-2 with an 8.25 ERA and a 1.92 WHIP in that span.

The Blue Jays come into the series 48-58 and in last place in the AL East, but they have gone 2-2 over their last four games. The Nationals just took two of three from the Diamondbacks to start their homestand and are 6-3 since the All-Star break. At 52-52, they continue to overachieve, and it makes sense that they’re the favorite on Monday night. However, with Scherzer on the mound and the Blue Jays’ batting order looking a little better over the weekend at Fenway, Toronto has a chance to pull off the upset.

Angels Moneyline (-107)

The Halos are slight underdogs at home as they welcome their division rivals from Houston. They aren’t quite plus-money plays on the money line, but they are still underdogs at this line. They’ll give the ball to Walbert Urena in the opener as they face Tatsuya Imai. The Angels avoided a sweep in San Francisco on Sunday with a 4-3 win, while the Astros couldn’t close out a sweep in Chicago, losing 12-3. They had won five straight before that defeat, though, while the Angels were 3-3 over their previous six.

The Angels’ big advantage (aside from home-field advantage) is that Urena has been more consistent than Imai. The 22-year-old righty is 6-7 with a 2.78 ERA and a 3.81 FIP in 18 games this season. He has allowed one or fewer runs in three straight starts. He holds a spotless 0.00 ERA across 6.2 innings against the Astros this year, though Houston roughed him up for six unearned runs out of the bullpen very early into the season. Still, he’s been much better lately and should be in position for another strong showing on Monday.

Imai has had a hard time adjusting to MLB in his first season after moving over from Japan. He is 6-4 with a 5.59 ERA and a 4.75 FIP. In his last three starts, he has allowed 11 walks and 12 hits in just 11 innings. He did get a win in his most recent outing against the Marlins, but he has been very volatile, with some very bad outings mixed in with stronger showings. The Angels got to Imai early in the year for four runs in 2.2 innings in his MLB debut.

Given the pitching matchup, the Angels have a solid chance to pull off an upset in the series opener despite their largely disappointing season.

Giants Moneyline (+113)

For the third option in Monday’s MLB underdog picks, let’s head to San Francisco, where the Giants will host the Brewers. They just missed out on the sweep of the Angels on Sunday, but they have won four of their last five home series dating back to before the All-Star break. The Giants are 24-26 at home compared to 20-35 on the road.

Starting pitcher Tyler Mahle echoes that trend with a 2-3 record in five home starts with a 3.00 ERA — but a 0-6 record on the road with an 8.05 ERA. In his last two home starts, he has allowed just one run over 12.2 innings against the A’s and Rockies. While he isn’t dominant, he does bring more upside than he seems to be getting credit for based on this moneyline.

He’ll be facing Milwaukee’s Brandon Sproat, who is 3-5 with a 5.09 ERA on the season. Over his last six starts, he’s only managed to get through 26.2 innings (just over 4 innings per start). While his strikeout numbers have been solid, he has a 4.42 FIP and a 1.38 WHIP and hasn’t been able to work deep into games. The Brewers have been very good since the break, going 7-2 in nine games, but all those contests were at home. In their last road series, they got swept in Pittsburgh.

For most of the season, the Brewers have been very good on the road, and they’re just one game behind the Dodgers for the best record in MLB. Still, since Mahle and the Giants have been much better at Oracle Park, they are a nice plus-money play as underdogs to start their series on Monday night.

If you choose to stack the three MLB underdog picks in this post into a parlay, you can get juicy +740 odds if the three picks run the table. Since they do come with plenty of risk, though, it also makes sense to play them individually and as a round robin, so that if any two of the three hit, you’ll still secure some serious payouts.

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.