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, here are my favourite dogs to back on Monday night — all at plus-money — on the DraftKings Sportsbook.
Best MLB Underdog Bets, Picks
Angels ML (+100)
While no one is mistaking the Angels for a World Series threat, the team has been quite solid so far in 2026, playing to an 11-12 record and touting the best run differential in the AL West (+11). Meanwhile, the Blue Jays were a World Series team, but injuries have pilled up early in the season, and the club has suddenly lost 13 of its last 18 games. Toronto will send Dylan Cease to the mound on Monday, but Los Angeles will counter with Reid Detmers, who seems like he might finally be figuring it out — I’m aware how often an MLB analyst has said that exact sentence. Through four starts, Detmers is in possession of a 2.53 xERA and a 2.47 FIP, as he’s struck out 26 opponents over 22.2 innings of work. He should have little issue with a Jays lineup that ranks 19th in wRC+ (99), 24th in ISO (.130) and 29th in expected wOBA on batted ball events (.344).
Astros ML (+102)
Houston has lost 12 of its last 14 games, but one of those two wins was Spencer Arrighetti’s first MLB start of the season. So, that’s something. It was a matchup with the Rockies away from Coors Field — which should be about as difficult as shooting fish in a barrel — and Arrighetti was more than up to the task, allowing a single earned run across six innings with 10 strikeouts. The Guardians will obviously present a more challenging opponent for Arrighetti on Monday, but it’s not like the team is the 1927 Yankees. Cleveland’s hit for power in 2026, yet it comes into tonight’s action sitting 23rd in average (.226) and 18th in wRC+ (18). Slade Cecconi won’t put fear into your heart, either. The 26-year-old sports a 5.03 ERA that completely validated by a 5.05 xERA. The Astros might be 8-15. However, they have the second-best lineup in baseball by wRC+ (122). Look for them to put up some crooked numbers versus Cecconi.
Reds ML (+102)
There’s a couple things we don’t know about this game. Namely, who is starting for the Rays. However, here’s what we do know. The Reds come into Monday having won five of their last six contests, and they currently sit first place in a surprisingly competitive NL Central. Cincinnati will start Rhett Lowder, the former seventh-overall pick in the 2023 MLB Draft. Lowder’s advanced statistics aren’t amazing, but the 24-year-old has maintained a 2.18 ERA and a 3.19 FIP in his 10 career starts in the big leagues. If nothing else, he’s proved he belong at this level. Then there’s the matchup. Tampa’s been good to start 2026, but I’m not sure how much longer that’s going to last with an offensive profile as putrid as the one the Rays are currently bringing to the table. The club ranks dead-last in barrel rate (4.4%), hard hit rate (33.5%) and expected wOBA on batted ball events (.334). “Rays Devil Magic” can only get you so far, right?
