MLB · 1 week ago

MLB Best Bets Today: Friday’s Top 2 Betting Picks (August 29)

Gabriel Santiago

Host · Writer

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There is no stopping us now. The MLB season and summer are fully underway, meaning there are betting opportunities every day between now and October. We’ve got you covered for Friday’s baseball schedule!

Where to Watch Milwaukee Brewers vs. Toronto Blue Jays

Ballpark: Rogers Centre
Location: Toronto, ON
Where to Watch: Sportsnet, FDSNWI, MLBN
Time: 7:07 p.m. ET
Spread: TOR -1.5 (+164) | Total: 7.5 (-115/-105)
Moneyline: MIL +112 | TOR -132

After an off day, the Toronto Blue Jays are back at home to host the Milwaukee Brewers. In what could be a 2025 World Series preview, we’ll see hurlers Shane Bieber and Freddy Peralta on the bump.

Both sides here are thriving this season, so we should be in store for an entertaining matchup. Bieber is back in action for his second start with Toronto since elbow surgery. Across the way, Peralta has compiled a 3.88 skill-interactive ERA (SIERA) throughout 147.2 innings.

Notably, the trend of overs at Rogers Centre is still going strong. The Blue Jays have been MLB’s best team for overs in 2025, showing a 75-53-6 (59.6%) record. That clip is even better for Toronto at home, where they have cashed the over at a 40-24-2 rate (62.5%).

The Brewers (.739) and the Jays (.769) both rank within the top-11 teams in terms of OPS. Despite the quality pitching in this one, these are quality lineups in action at a hitter’s park. Going against a small number like 7.5 runs, I am comfortable letting it ride with the over in Canada.

Best Bet: Over 7.5 (-115)

Where to Watch Pittsburgh Pirates vs. Boston Red Sox

Ballpark: Fenway Park
Location: Boston, MA
Where to Watch: SNP, NESN, MLBN
Time: 7:10 p.m. ET
Spread: PIT -1.5 (+168) | Total: 8 (-104/-118)
Moneyline: PIT -102 | BOS -116

Out at historic Fenway Park, we’ll see two of MLB’s oldest franchises getting after it in the Pittsburgh Pirates and Boston Red Sox. Paul Skenes will go for Pittsburgh, while Boston has not named a starter at the time of authorship.

Skenes has been spectacular in the current campaign. FanDuel Sportsbook lists him as the overwhelming odds-on favorite (-10000) to win the 2025 National League Cy Young award—and deservedly so. Skenes is striking out 10.12 hitters per nine innings in addition to boasting a 2.40 FIP. Conversely, the Red Sox will likely dip into their bullpen, which has been quite good this season.

With their ace on the hill, I believe the Pirates can get the win in enemy territory. Pittsburgh features seven victories over its last 10 outings. Also, the Buccos have gotten hot as of late. They displayed an .818 team OPS throughout the past week.

If Skenes can bring his usual stuff, I’m confident that the Pirates can scrap this one out in Boston. It should be a tight contest, but considering Pittsburgh is listed with -102 moneyline odds on Skenes’ day, I am willing to roll the dice.