Daily Dingers for Monday (Sept 14th): Best & Most Fun Home Run Bets

We’ve got a short slate at the diamond to kick off the week, but we’re still going to cash some bets. For my Daily Dingers for Monday (Sept 14th): Best & Most Fun Home Run Bets, we’re off to Wrigley Field in Chicago, Illinois, and Target Field in Minneapolis, Minnesota. Let’s get this money!

Daily Dingers for Monday (Sept 14th): Best & Most Fun Home Run Bets

Atlanta Braves vs Chicago Cubs

Start Time: 7:40 PM EST

I’m not taking any wild swings on my home run plays for Monday – all three players are guys who are known to hit the ball out of the park. And this season, few (three to be exact) have done that more than Atlanta Braves slugger Matt Olson.

Olson has 39 dingers now after going yard on Sunday, tied for his second-best total in a season. He likes hitting against tomorrow’s starter, David Peterson, with four career home runs, so I like his chances to reach 40 on Monday.

Best Bet: Matt Olson (+434)

New York Yankees vs Minnesota Twins

Start Time: 7:40 PM EST

New York Yankees legend Aaron Judge, however, won’t be joining the 40-home run club this season, but that’s only because injuries have limited him to 64 games played thus far.

I do like Judge to get homer #18 tomorrow night in the Twin Cities, though. Judge is another guy who likes his pitching matchup on Monday, as he’s gone deep four times in 17 career at-bats against the Minnesota Twins’ Dean Kremer.

Best Bet: Aaron Judge (+300)

Bonus Bet: Fernando Tatis Jr. (+280)

2026 Overall Record: 36-194 (16%)
Profit (based on $100/bet): -($2,312.00)
Return on Investment: -10%