Red Sox vs. Yankees Prediction & Picks: MLB Odds for Saturday, Aug. 29
Last Updated: August 29, 2026 9:02 AM EDT • 4 minute read X Social Google News Link
The New York Yankees and Boston Red Sox are on a collision course to meet in the playoffs, and the rivalry has been competitive with the teams splitting the 10 head-to-head matchups so far. My Red Sox vs. Yankees prediction for the second game of the doubleheader likes the road underdog’s chances of pulling the upset, even though it's a Bronx Bomber I'm backing to go deep with the last of my MLB picks.
Max Fried makes his first start off the injured list, while the Red Sox did not announce their starting pitching plans as of this writing. First pitch from Yankee Stadium scheduled for 7:15 p.m. ET (FOX). The Yankees are -130 betting favorites.
⚾ Red Sox vs. Yankees picks & odds today
See all of our experts’ MLB picks based on the latest MLB odds;
| ⚾ Pick | 💵 Units | 📝 Notes |
|---|---|---|
| Red Sox ML (+118 via FanDuel) | 1u → 1.18u | Boston has been MLB's best team since the All-Star Break |
| Trent Grisham to hit a home run (+500 via FanDuel) | 0.25u → 1.25u | Bellinger is one of MLB's best hitters in lefty-lefty matchups |
Total wagered: 1.25 units | Max profit: 2.43 units
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🏆 Who will win Red Sox vs. Yankees?
I like Boston’s chances off pulling the upset in the second game of the doubleheader given the advantages it has in the bullpen.
Score prediction: Red Sox 6, Yankees 4
💰 Red Sox vs. Yankees prediction & best bet
Red Sox ML (+118)
Anytime two teams meet in a twin bill it puts an emphasis on the bullpen, which is one area where the Red Sox have a clear advantage.
Since July 1, Boston’s relievers lead the Majors in ERA and FIP, and lead all AL bullpens in HR/9 rate and WAR.
The Red Sox have also had their share of success against the Yankees, winning four straight in the rivalry, and 13 of the last 20 at Yankee Stadium. They are an MLB-best 27-12 since the All-Star Break, and Roman Anthony’s return only strengthens a deep and powerful lineup.
📡 SBR Edge: Bucking a doubleheader trend
If Boston wins the second game of the doubleheader, it would improve to 2-1 in such games, and would also be New York's first loss in that split (2-0 entering today).
💣 Red Sox vs. Yankees home run prediction
Trent Grisham to hit a home run (+500)
It is difficult to provide any solid analysis on home run wagers with Boston not having announced its starting pitching plans. But given the fact that Max Fried has allowed just two home runs in 86 1/3 innings this year, I am certainly not rushing to the betting window to back any Red Sox sluggers to go yard.
Trent Grisham has heated up with the weather staying warm, as his seven home runs in August are his highest for a single month this season. Though he has just two hits in his last 22 at-bats, one was a home run, which also make up three of his last eight hits overall.
Grisham is always a solid candidate to take advantage of Yankee Stadium's short porch. He is one of the few Yankee sluggers to rank in the 77th percentile or higher in average exit velocity and hard-hit rate, the latter of which is on pace to be above 46% for the third straight season.
🚀 Red Sox vs. Yankees same-game parlay
The lack of player prop availability and the fact that these wagers were somewhat dependent on the first game of today's doubleheader's results means I'm only adding two legs to this same-game parlay. Because of that, I am getting more aggressive leaving Grisham's home run odds as a part of this wager, whereas I normally get more conservative with player prop wagers that I include in SGPs.
💵 Red Sox vs. Yankees SGP picks
- Yankees ML (+118)
- Trent Grisham to hit a home run (+500)
Best odds: +1208 via FanDuel (0.1u -> 1.21u)
💵 My betting record for MLB picks
All MLB picks, including SGPs, have been tracked since March 26.
| Bet type | Record | Net profit | ROI |
|---|---|---|---|
| Overall | 247-405-1 | +46.70 units ✅ | +11.5% ✅ |
| Game picks | 97-73-1 | +17.07 units ✅ | +7.3% ✅ |
| Player props | 150-332 | +29.63 units ✅ | +12.7% ✅ |
💡 How I'm betting Red Sox vs. Yankees: MLB strategy
Follow all of our MLB analysis and expert predictions for baseball season.
It isn’t often that one can back a team that has been the best in baseball in the second half of the season at these moneyline odds. Oddly enough, this would be a lot more confident of a wager if the Red Sox were to drop the first game of the doubleheader given how difficult it is to sweep a twin bill. I will also be looking into Max Fried props when they become available, specifically the Under of 15.5 outs recorded as I expect the Yankee coaching staff to keep him on a short leash with this being his first start off the IL.
📊 Live Red Sox vs. Yankees odds
These lines have a lot of room for change, and will likely adjust based off of what happens in today's doubleheader. For now, the Yankees are slightly bigger favorites in the game Max Fried is starting than the first game of the twin bill that sees Carlos Rodon toeing the rubber. DraftKings is also the only top sports betting site offering an O/U of 8 while the rest of the market is at 7.5. But I expect more will align with DraftKings at the higher total before first pitch, as the betting splits are 62/38 in favor of the Over.
📈 Red Sox vs. Yankees betting trends
| Red Sox | Statistic | Yankees |
|---|---|---|
| 73-61 | W-L record | 76-58 |
| 68-65 | Run line record | 66-68 |
| 62-69-3 | O/U record | 56-75-3 |
| 7-3 | Last 10 games | 7-3 |
| 3.46 | Team ERA | 3.22 |
| .249 | Team batting avg. | .230 |
| .728 | OPS | .717 |
🚑 Red Sox vs. Yankees injuries
📺 How to watch Red Sox vs. Yankees
- Date: Friday, August 28
- First pitch: 7:15 p.m. ET
- Ballpark: Yankee Stadium (Bronx)
- Streaming: Apple TV
- Red Sox starter: Undecided
- Yankees starter: Max Fried (4-4, 2.81 ERA)
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