Pirates vs. Red Sox Prediction, Odds & Expert Picks: MLB Best Bets for Aug. 29

Will we get a pitcher's duel tonight with Cy Young favorite Paul Skenes up against top prospect Payton Tolle?

Mike Spector

Last Updated: August 29, 2025 9:25 AM EDT • 6 minute read

Pirates vs. Red Sox Prediction, Odds & Expert Picks: MLB Best Bets for Aug. 29 — Pictured: Pittsburgh Pirates starting pitcher Paul Skenes pitches as I make my best Pirates vs. Red Sox prediction. Photo by Charles LeClaire via Imagn Images.

It's must-watch television tonight when National League Cy Young Award frontrunner and Pittsburgh Pirates ace Paul Skenes opposes Payton Tolle, top pitching prospect for the Boston Red Sox, and I break it down with my Pirates vs. Red Sox prediction.

First pitch from Fenway Park in Boston set for 7:10 p.m. ET (MLBN) is part of our MLB picks. Oddsmakers peg this interleague clash as a virtual pick 'em with each team at -110 moneyline odds. Even though I am backing Boston to win this series opener, I am calling for another solid outing from Skenes, and certainly don't have any picks against him in my home run predictions today.

⚾ Pirates vs. Red Sox expert picks & predictions

MLB expert picks made Friday; odds subject to change.

Moneyline pick: Red Sox (-104 via FanDuel) ⭐⭐⭐⭐
Run line pick: Red Sox +1.5 (-178 via FanDuel) ⭐⭐⭐⭐⭐
Over/Under pick: Under 8 (-115 via BetMGM) ⭐⭐⭐⭐

📝 Pirates vs. Red Sox preview & best bet

Track the latest MLB scores for line movement and matchup info.

🧦 Red Sox moneyline (-104) ⭐⭐⭐⭐

Paul Skenes is a virtual lock to win according to the NL Cy Young Award odds, with a 98.04% implied probability through DraftKings’ -5000 odds. But he is also under .500 on the season for a reason, as his lineup often fails to provide him with run support. Thus, I am backing a Boston outright victory over Pittsburgh with my Pirates vs. Red Sox prediction.

Boston just finished an eight-game road trip with a 7-1 record, having won three of its previous four series while moving a season-high 15 games over .500. Its pitching was a key reason for its recent road success, compiling a near 2.00 team ERA over the eight games.

I expect Payton Tolle, a 6-foot-6 southpaw to match zeros with Skenes. He posted a 28.8% strikeout rate and 69.9% strike rate while throwing just 15 innings at the Triple-A level.

With most of the best MLB betting sites offering Boston’s moneyline odds at -110 (carrying a 52.38% implied probability), I am getting a great price at FanDuel with its -104 odds that returns $9.62 in profits on a winning $10 wager.

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💰 Best Pirates vs. Red Sox player prop bet

Our MLB player prop odds tool shows the best odds for every market across legal sportsbooks in your area.

🔥 Paul Skenes Under 1.5 earned runs (+140) ⭐⭐⭐

Skenes leads the league in ERA (2.07), FIP (2.40), ERA+ (205) and home runs per nine innings (0.5). Perhaps even more impressive are his OBA splits against certain pitches, with opponents batting .143 against his sweeper and .096 against his changeup.

Had Boston slugged its way to a series sweep of the Baltimore Orioles, I would have opted for a different best Pirates vs. Red Sox player prop. But the Red Sox averaged fewer than four runs per game in the hitter-friendly Camden Yards, and have scored just 19 runs in their last five games. Thus, I am backing Skenes to dominate in what should be an electric atmosphere at Fenway Park.

Skenes has the second-lowest ERA through 50 career starts of any pitcher since 1920, so the fact that we can back him at plus-money odds for this wager is an incredible value. The +140 odds at Caesars beat the +130 odds (carrying a 43.48% implied probability) at the low end of the market, and return $14 in profit on a winning $10 wager.

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📊 Pirates vs. Red Sox odds: Aug. 29

MLB odds update live in real time.

📈 Pirates vs. Red Sox betting odds analysis

Pittsburgh’s -1.5 runline has stayed relatively firm at its opening number of +155. It now ranges from +152 at FanDuel and bet365 to +158 at Caesars. The Over/Under is set at 8 runs, with the Under slightly more juiced to -115, which suggests the total could tick down to 7.5 or lower before first pitch.

🔢 Pirates vs. Red Sox stats

Season stats courtesy of baseball-reference.com.

Pirates (59-76)	Statistic (per game)	Red Sox (75-60)
3.6	Runs	4.96
7.7	Hits	8.65
.234	AVG	.252
.352	SLG	.425
.657	OPS	.749
3.93	ERA	3.67
8.04	K/9	8.31
2.88	BB/9	3.26
0.97	HR/9	1.02

🚑 Pirates vs. Red Sox injuries

📺 Pirates vs. Red Sox game info

When: Friday, Aug. 29
First pitch: 7:10 p.m. ET
Where: Fenway Park (Boston)
How to watch: MLB Network

💡 Expert MLB predictions today

❓ Pirates vs. Red Sox FAQs

Who is favored to win Pirates vs. Red Sox?

There is no favorite in this Pirates vs. Red Sox game, as oddsmakers have pegged it as a virtual pick 'em with both teams at -110 moneyline odds.

What is the run line for Pirates vs. Red Sox?

Pittsburgh’s -1.5 odds are at +155, while Boston’s +1.5 odds are at -190 on the high end of the market.

What is the Over/Under for Pirates vs. Red Sox?

The top sports betting sites have the O/U at 8.0 runs, juiced to -105 for the Over and -115 to the Under.

What are the best bets for Pirates vs. Red Sox?

My Pirates vs. Red Sox best bets back Boston to win outright with Paul Skenes going Under his projected 1.5 earned runs total.

When is the Pirates vs. Red Sox game?

The Pirates vs. Red Sox first pitch is set for 7:10 p.m. ET, airing on MLBN.

How do baseball odds work?

When betting on MLB, the run line shows how many runs the favorite needs to win by in order to cash the bet. For example, a favorite of -1.5 must win by two or more runs to cover the run line, while an underdog at +1.5 must win outright or lose by one run to cover the run line.

Moneyline odds represent the payout for picking the outright winner (+200 means a $100 bet wins $200, while -200 means a $200 bet wins $100). Over/Unders let you wager on whether the combined total of runs will be higher or lower than the set number.

You can determine the payouts and implied probabilities for any wager - or convert odds to different formats - with our odds converter.

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Written by:
Mike Spector

Mike started in the sports writing industry in July 2019, and gained a lot of followers in his first year after finishing with the No. 2 overall record in an annual NFL betting competition, which made picks against the spread, and from an Over/Under and moneyline perspective. Mike is an avid fan of the NFL, MLB, tennis, and all college sports. In his opinion, March Madness is the best sporting event there is, and he's especially euphoric starting with conference tournament time in college basketball. Mike's a big advocate of "fading the public" and making plays that are contrarian, constantly citing that "there are reasons why they have those big shiny buildings in Las Vegas." When making wagers, Mike leans on his NFL experience and always scours the best odds at all of the major sports betting sites, where he mostly sifts through DraftKings, FanDuel, BetMGM, and bet365. He's tried several others and is of the firm belief that bettors should not just stick to one sportsbook, as there is always likely better value to be had with the same wager. In addition, while Mike received his undergraduate degree from Villanova University, he has no issue betting against the Wildcats when it comes to college basketball wagering, and suggests other bettors should always put their “head” before their “hearts.”