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Casey Wilson's best MLB player prop bets for today (9/29/2025). Bet his home run props (HR props) and win money betting on MLB player props, including Riley Greene, Fernando Tatis Jr., Aaron Judge and Freddie Freeman.
We have four games this Tuesday in MLB to open up our Wild Card round. What better day for a playoff home run article than "Dinger Tuesday?" With the playoffs beginning, home runs are going to become rarer. I am going to give you my favorite home run from each playoff game today. I would advise scaling back on the betting size for home runs in the playoffs.
I will provide my four favorite home run bets on today’s slate. I do not recommend betting any more than four home runs, as it will be tough to sustain a bankroll. My favorite way to bet home runs is to round-robin them, which I will do tonight. I've put a small unit size on these, but I want the opportunity to cash in bigger if more than one home run is hit.
Below, you'll read about my favorite home run props from MLB games on Tuesday, September 29, 2025. Odds for each pick are from DraftKings Sportsbook and are subject to change throughout the day. Remember to always shop around at other sportsbooks for the best price so you can get more value on your wagers. Odds can vary significantly from one sportsbook to another.
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MLB Prop Bets - Today's Home Run Prop Picks (9/29/2025)
Here are all the hitters I'll cover for HR props on Tuesday, September 29:
- Riley Greene, Detroit Tigers
- Fernando Tatis Jr., San Diego Padres
- Aaron Judge, New York Yankees
- Freddie Freeman, Los Angeles Dodgers
Riley Greene OVER 0.5 Home Runs (+520 FanDuel)
Being from Cleveland, my first home run bet of the day pains me to write because I will be rooting hard for the Guardians. Of course, I do not want to attack Tarik Skubal. I will be going against Gavin Williams in this spot.
Williams will toe the rubber at home at Progressive Field tonight, which is a park that is more favorable for left-handed hitters. It will be in the low 70s with a 10-plus wind blowing in, making it ideal pitching conditions.
Williams, on the season, has allowed a 1.23 HR/9, 36.1% FB, and a 33.0% Hard Hit. Over his last two starts, he has allowed a 42.1% FB and a 42.1% Hard Hit. Left-handed hitters have been the better split against Williams in 2025. He has allowed 13 home runs with a .323 SLG, .160 ISO, 12.2% Brl, and a 46.4% Hard Hit.
Riley Greene leads the Tigers with 36 long balls on the season. He has hit 32 of those against right-handed pitching, where he is slashing .276/.325/.564 with a .890 OPS. No one on this Tigers team is swinging a hot bat, but Greene has two home runs over the last 10 days.
The intriguing thing here is Greene hits everything that Williams throws, as seen below. In particular, Williams has allowed eight home runs off his four-seamer to left-handed hitters, and Green has nine home runs against that pitch with a .474 SLG and a .230 ISO.
Fernando Tatis Jr. OVER 0.5 Home Runs (+448 DraftKings)
Our second home run bet of the day will take place at Wrigley Field, where there will be a 5-10 mph wind blowing in. In this park, it makes a significant difference, but the wind can change in a second at this park, and it plays much more hitter-friendly during the day.
Nick Pivetta will square off against Matthew Boyd, who both have been prone to the long ball. Matthew Boyd will be our target here because of how his splits line up against the splits of this Padres offense.
Boyd has allowed a 1.37 HR/9, 51.8% FB, and a 33.3% Hard Hit over the last 30 days. He has allowed a 2.16 HR/9, 53.8% FB, and a 38.5% Hard Hit over his previous two starts. Right-handed hitters have been the way to attack Boyd in 2025. He has allowed 17 home runs with a .395 SLG, .158 ISO, 10.7% Brl, and a 39.3% Hard Hit against the split.
This Padres team is full of right-handed power bats, but their two superstars lead them which is Fernando Tatis and Manny Machado. Tatis is second to Machado with 25 home runs this season. He has hit 5 of those against left-handed pitching. Tatis is on a hot streak at the moment. He has three home runs over the last ten days and is slashing .333/.357/.667 with a 1.024 OPS.
Boyd has allowed 10 home runs against his four-seam fastball to right-handed hitters this season. Tatis has a .448 SLG, .172 ISO, and three home runs off that pitch from southpaws in 2025.
Look for Tatis to hit something far enough to go through the wind over the ivy.
Aaron Judge OVER 0.5 Home Runs (+230 FanDuel)
Our third bet will be from one of my favorite series to watch between the rivals, the Red Sox and Yankees. The Yankees will host the Red Sox at Yankee Stadium. We have another typical late-September game with the wind blowing in and cold temperatures on the East Coast.
I don't love much from this game, but Crochet does give up the long ball, and Aaron Judge against a left-hand pitcher is always automatic, so I cannot pass this spot up even at the short odds.
On the season, Crochet has allowed a 1.05 HR/9, 33.8% FB, and a 32.4% Hard Hit. Over the last thirty days, he has allowed a 2.18 HR/9, 32.5% FB, and a 36.3% Hard Hit. He has allowed 24 home runs this season, and 21 of those have come against right-handed hitters. He has allowed a .374 SLG, .146 ISO, 10.5% Brl, and a 40.2% Hard Hit against the split in 2025.
Judge leads the Yankees and is second in the American League in home runs with 53. He has a .689 SLG and a 1.147 OPS this season. Judge has 16 home runs against left-handed pitching this season and has a .795 SLG and a 1.292 OPS.
Aaron Judge's final 2025 numbers jump off the page 😮 pic.twitter.com/mpPLO6eD5f
— MLB (@MLB) September 29, 2025
Crochet has allowed 16 of his home runs this season to right-handed hitters off two pitches, which are his four-seamer and his cutter. The four-seamer has a .480 SLG and 11 home runs against it, while the cutter has a .403 SLG and five home runs against it. Judge has a .816 SLG, .553 ISO against the four-seamer, and a 1.692 SLG and a 1.000 ISO against the cutter.
The matchup is too good to pass up for Judge in this spot.
Freddie Freeman OVER 0.5 Home Runs (+392 DraftKings)
Playoff Freddie is back. This dude was electric in the World Series and playoffs last season, and I am going right back to the well in a great spot.<
FREDDIE FREEMAN GOES BACK-TO-BACK! #WORLDSERIES pic.twitter.com/xwRHRb3IoM
— MLB (@MLB) October 27, 2024
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The Dodgers will host the Reds tonight in the last game of the day, and Hunter Greene will square off against Blake Snell. Greene and Snell have both been dynamite, but I like some of the splits I am seeing for the Dodgers off Greene, and this team was elite at home in the playoffs in 2024.
Greene, on the season, has a 1.25 HR/9, 48.8% FB, and a 31.9% Hard Hit. Lefties have hit nine home runs off him this season, including a .384 SLG, .200 ISO, 15.7% Brl, and a 58.7% Hard Hit.
Free money Freddie has 24 home runs this season. He has hit 16 of those off right-handed pitching and is slashing .299/.374/.500 with a .874 OPS against the split. He has three home runs and a .581 SLG over the last 10 days, so he is in incredible form as well.
Whenever Freddie Freeman gets postseason at-bats, play him. This spot is no different.
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