Our man with the home run bets has taken a little bit of a break to recharge the batteries and I’ll be stepping in to pinch hit. We’ll look to build his bankroll back up on this column for a couple of days with some long ball, long shot odds. For my Daily Dingers for Friday (August 30th): Best & Most Fun Home Run Bets, we’ll take a look at a couple divisional rivalry games. Come check out these home run prop bets!
Daily Dingers for Saturday (August 30th): Best & Most Fun Home Run Bets
Cincinnati Reds vs Chicago Cubs
Start Time: 7:20 PM EST
Maybe I’m not splitting the atom on wanting to get behind the mustachioed Rookie of the Year candidate out of Cincinnati, but Sal Stewart is in a great spot on Sunday. Shota Imanaga is on the hill for the Cubs and he’s been loving every interaction with him. In six career at bats, Stewart has three hits and a dinger off of the lefty.
In addition, the wind is going to be blowing out heavily at Wrigley Field. The forecast calls for 15 mile per hour winds out to left field and he should be able to pull one down that line.
Best Bet: Sal Stewart (+300)
Boston Red Sox vs New York Yankees
Start Time: 1:35 PM EST
Speaking of favorable conditions for a dinger, you always have to love the bread box that is Yankee Stadium. We’re seeing calls for up to 10 mile per hour winds in New York on Sunday afternoon, which means we should see a couple of balls flying out.
If someone is going to do the heavy lifting for one of these teams, why not Wilson Contreras? He’s been without a homer for a few games, but has one against Will Warren in just two career at bats. The Red Sox could use an offensive boost and Contreras has been the guy to give it to them this year.
Best Bet: Wilson Contreras (+390)
Bonus Bet: Cal Raleigh (+290)
2026 Overall Record: 32-168 (16%)
Profit (based on $100/bet): -($1,567.00)
Return on Investment: -8%
**Results pending Saturday’s games**
SGPN Daily Content for August 30th, 2026
Don’t Forget About our free picks pages, too!
COLLEGE BASKETBALL PICKS – THE PICKS POWERHOUSE
SOCCER PICKS – KICK IT ON THE PITCH
