Division Series Daily Dingers for Wednesday (Oct 7th): Best & Most Fun Home Run Bets

Freddie Freeman has quickly become my favorite baseball player after cashing another huge (+614) home run prop on him. For my Division Series Daily Dingers for Wednesday (Oct 7th): Best & Most Fun Home Run Bets, we’re off to Rate Field in Chicago, Illinois, and Yankee Stadium in the Bronx, New York. Let’s get this money!

Division Series Daily Dingers for Wednesday (Oct 7th): Best & Most Fun Home Run Bets

Cleveland Guardians vs Chicago White Sox

Start Time: 4:00 PM EST

We start things in Chi-town, as the Chicago White Sox look to complete the three-game sweep of their hated divisional rivals, the Cleveland Guardians. And I expect the Sox’s Miguel Vargas to help that cause tomorrow.

Vargas had a breakout season this year, swatting 33 dingers. While he has yet to go yard in the playoffs, he does have a homer in only two at-bats against Game 3’s starter, Daniel Espino.

Best Bet: Miguel Vargas (+520)

Tampa Bay Rays vs New York Yankees

Start Time: 8:00 PM EST

The New York Yankees’ Austin Wells has come up in my home run prop plays a couple of times in the playoffs, and he’s coming up again tomorrow as the Yankees fight for their playoff lives against the visiting Tampa Bay Rays.

Wells has had success batting against Rays’ starter Nick Martinez, with two career homers in five at-bats, so I’m going with him again.

Best Bet: Austin Wells (+562)

Bonus Bet: Freddie Freeman (+660)

2026 Playoffs Overall Record: 5-13 (28%)
Profit (based on $100/bet): $1,164.00
Return on Investment: 65%