Pittsburgh Pirates vs Boston Red Sox Prediction & Picks - MLB

USA - MLB

Pittsburgh Pirates
8/29/25 19:10
Boston Red Sox

Prediction:

 

UNDER 8

-115
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 by Travis Pulver in MLB Picks

The Pittsburgh Pirates will be in Massachusetts this weekend for a three-game series with the Boston Red Sox. Game One of the series is scheduled for today in Fenway Park at 7:10 p.m. EST. Fans can watch the action unfold via the MLB Network. Boston comes into the series fresh off a four-game sweep of the Orioles in Baltimore to improve to 75-60. They are in firm control of a wild card spot but only 3.5 games back in the AL East. It’s been a rough season for the Pirates, who are 59-76, but they’ve been playing good baseball lately. While they lost their last game, 4-1 vs. the Cardinals, they’ve won seven of their last ten.

Pittsburgh will have a definite advantage on the mound. The Pirates are scheduled to start Paul Skenes, who is 8-9 in 27 starts with a 2.07 ERA, .94 WHIP, and .195 OBA. Skenes has gone 3-5 on the road in 14 starts with a 2.50 ERA and .201 OBA. As for Boston, the Red Sox are calling up Payton Tolle to start. Tolle is an imposing 6-foot-6, 250-pound player with a killer fastball. He is the No. 2 prospect in the Boston farm system and No. 28 in baseball. IN Triple-A, he’s pitched 15 innings (3.06 ERA) and struck out 17 while walking just two.

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Pittsburgh Pirates vs Boston Red Sox Form

Table

Teams % P W L
8
Boston Red Sox
Boston Red Sox
0.556 135 75 60
27
Pittsburgh Pirates
Pittsburgh Pirates
0.437 135 59 76

Pittsburgh Pirates and Boston Red Sox Latest Matches

Pittsburgh Pirates
Pittsburgh Pirates Latest matches
W W L W W L
Victories

4/6 (67%)

Defeats

2/6 (33%)

Aug 28, 2025 - MLB

Pittsburgh Pirates
1 :  4
St. Louis Cardinals

Aug 27, 2025 - MLB

Pittsburgh Pirates
2 :  1
St. Louis Cardinals

Aug 26, 2025 - MLB

Pittsburgh Pirates
8 :  3
St. Louis Cardinals

Aug 25, 2025 - MLB

Pittsburgh Pirates
6 :  7
St. Louis Cardinals

Aug 24, 2025 - MLB

Colorado Rockies
0 :  4
Pittsburgh Pirates

Aug 23, 2025 - MLB

Colorado Rockies
1 :  5
Pittsburgh Pirates
W L W W W W
Victories

5/6 (83%)

Defeats

1/6 (17%)

Aug 24, 2025 - MLB

Colorado Rockies
0 :  4
Pittsburgh Pirates

Aug 23, 2025 - MLB

Colorado Rockies
1 :  5
Pittsburgh Pirates

Aug 22, 2025 - MLB

Colorado Rockies
0 :  9
Pittsburgh Pirates

Aug 20, 2025 - MLB

Toronto Blue Jays
1 :  2
Pittsburgh Pirates

Aug 19, 2025 - MLB

Toronto Blue Jays
7 :  3
Pittsburgh Pirates

Aug 18, 2025 - MLB

Toronto Blue Jays
2 :  5
Pittsburgh Pirates
L L L W W L
Victories

2/6 (33%)

Defeats

4/6 (67%)

Aug 28, 2025 - MLB

Pittsburgh Pirates
1 :  4
St. Louis Cardinals

Aug 27, 2025 - MLB

Pittsburgh Pirates
2 :  1
St. Louis Cardinals

Aug 26, 2025 - MLB

Pittsburgh Pirates
8 :  3
St. Louis Cardinals

Aug 25, 2025 - MLB

Pittsburgh Pirates
6 :  7
St. Louis Cardinals

Aug 17, 2025 - MLB

Pittsburgh Pirates
3 :  4
Chicago Cubs

Aug 16, 2025 - MLB

Pittsburgh Pirates
1 :  3
Chicago Cubs
Boston Red Sox
Boston Red Sox Latest matches
W L W W W W
Victories

5/6 (83%)

Defeats

1/6 (17%)

Aug 28, 2025 - MLB

Boston Red Sox
3 :  2
Baltimore Orioles

Aug 27, 2025 - MLB

Boston Red Sox
3 :  2
Baltimore Orioles

Aug 26, 2025 - MLB

Boston Red Sox
5 :  0
Baltimore Orioles

Aug 25, 2025 - MLB

Boston Red Sox
4 :  3
Baltimore Orioles

Aug 24, 2025 - MLB

Boston Red Sox
2 :  7
New York Yankees

Aug 23, 2025 - MLB

Boston Red Sox
12 :  1
New York Yankees
L W W L L L
Victories

2/6 (33%)

Defeats

4/6 (67%)

Aug 19, 2025 - MLB

Baltimore Orioles
4 :  3
Boston Red Sox

Aug 18, 2025 - MLB

Baltimore Orioles
6 :  3
Boston Red Sox

Aug 17, 2025 - MLB

Miami Marlins
5 :  3
Boston Red Sox

Aug 16, 2025 - MLB

Miami Marlins
5 :  7
Boston Red Sox

Aug 15, 2025 - MLB

Miami Marlins
1 :  2
Boston Red Sox

Aug 6, 2025 - MLB

Kansas City Royals
7 :  3
Boston Red Sox
W L W W W W
Victories

5/6 (83%)

Defeats

1/6 (17%)

Aug 28, 2025 - MLB

Boston Red Sox
3 :  2
Baltimore Orioles

Aug 27, 2025 - MLB

Boston Red Sox
3 :  2
Baltimore Orioles

Aug 26, 2025 - MLB

Boston Red Sox
5 :  0
Baltimore Orioles

Aug 25, 2025 - MLB

Boston Red Sox
4 :  3
Baltimore Orioles

Aug 24, 2025 - MLB

Boston Red Sox
2 :  7
New York Yankees

Aug 23, 2025 - MLB

Boston Red Sox
12 :  1
New York Yankees

Pittsburgh Pirates against Boston Red Sox : Head to Head (H2H)

Pittsburgh Pirates

17 %

Boston Red Sox

83 %

Mar 21, 2025 - MLB Spring Training

Pittsburgh Pirates
1 :  2
Boston Red Sox

Mar 4, 2025 - MLB Spring Training

Boston Red Sox
12 :  4
Pittsburgh Pirates

Apr 21, 2024 - MLB

Boston Red Sox
6 :  1
Pittsburgh Pirates

Apr 20, 2024 - MLB

Boston Red Sox
4 :  2
Pittsburgh Pirates

Apr 19, 2024 - MLB

Boston Red Sox
8 :  1
Pittsburgh Pirates

Apr 3, 2023 - MLB

Pittsburgh Pirates
7 :  6
Boston Red Sox

Pittsburgh Pirates - Boston Red Sox Key Points

  1. Boston leads the all-time series vs. Pittsburgh 18-14.
  2. They swept the Pirates in Pittsburgh last year (3-0) but got swept the year before at home (0-3).
  3. Skenes gave up four earned runs in each of his last two road starts (vs. Milwaukee, Aug. 12; vs. Colorado, Aug. 2).
  4. Betting Public: 9% of TOTAL tickets and 10% of the handle are on the UNDER (8).
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Our Pittsburgh Pirates vs Boston Red Sox Prediction

I don’t see why the public is going so heavy on the OVER. Skenes is one of the best pitchers in baseball. His last two road starts were not great, but more often than not, he dominates opposing lineups. Boston is not hitting so well right now that there is reason to think the Red Sox will score much. If the Pirates had been hitting over .300 for the last week like the Rangers, I might be concerned about Boston’s rookie pitcher making his first MLB start. But his resume is good enough for me to believe he’ll be fine against a lackluster Pirates lineup.

Our Pirates vs. Red Sox Pick: UNDER 8

Prediction:

 

UNDER 8

-115
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All tips are fully researched and given in good faith, but profits cannot be guaranteed.

Pittsburgh Pirates vs Boston Red Sox Picks
Up to $250 to bet on Pittsburgh Pirates - Boston Red Sox! 

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