Division Series Daily Dingers for Monday (Oct 5th): Best & Most Fun Home Run Bets

You know how yesterday I bragged about having a 50% return on investment for my home run bet in the playoffs? Well, hold my beer – it’s now 73% after Freddie Freeman went yard for a +650 score on Sunday. For my Division Series Daily Dingers for Monday (Oct 5th): Best & Most Fun Home Run Bets, we’re off to Progressive Field in Cleveland, Ohio, and Tropicana Field in St. Petersburg, Florida. Let’s get this money!

Division Series Daily Dingers for Monday (Oct 5th): Best & Most Fun Home Run Bets

Chicago White Sox vs Cleveland Guardians

Start Time: 5:00 PM EST

Japanese rookie Munetaka Murakami had an impactful first season in the majors with the Chicago White Sox, leading the team with 35 dingers. And while he struggled in their Wild Card sweep of the Houston Astros, MM came alive in Game 1 of the ALDS, hitting a dinger.

And I like Murakami’s chances of making it two straight games with a homer. The Cleveland Guardians are starting Gavin Williams in Game 2, and he was among the majors’ leaders in homers allowed this season. Plus, Murakami has taken him yard this year already.

Best Bet: Munetaka Murakami (+450)

New York Yankees vs Tampa Bay Rays

Start Time: 8:00 PM EST

For the night game, I’ve got a less obvious pick, as the New York Yankees’ Austin Wells is definitely not a slugger (he only managed 14 dingers this season). However, there is a method to my madness.

Wells got the Bronx Bombers’ only hit in Game 1, plus he homered in the Yankees’ last regular-season game against the Tampa Bay Rays. Also, Wells has homered in only four career at-bats against Game 2’s starting pitcher, Freddy Peralta.

Best Bet: Austin Wells (+740)

Bonus Bet: Miguel Vargas (+700)

2026 Playoffs Overall Record: 4-9 (31%)
Profit (based on $100/bet): $950.00
Return on Investment: 73%