Boston Red Sox vs Pittsburgh Pirates Prediction, Preview and Odds - 08/14/2026

Game Time: 6:40 pm ET, Friday, August 14, 2026

Venue:  PNC Park, Pittsburgh, PA 

Where to Watch:  MLB TV

DraftKings:  Moneyline odds:  Red Sox -149, Pirates +123; Over/Under:  8 runs

Bet365:  Moneyline odds:  Red Sox -150, Pirates +125; Over/Under:  8 runs

BetMGM:  Moneyline odds:  Red Sox -140, Pirates +115; Over/Under:  8 runs

Boston Red Sox:  64-56 (3rd place, AL East)

Pittsburgh Pirates:  59-64 (5th place, NL Central)

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Boston Red Sox:  5-5 last 10

Pittsburgh Pirates:  3-7 last 10

The Red Sox are entering this series off a win and lost their 4-game series against the Toronto Blue Jays 3-1 in their last series. They enter this game with a 64-56 record overall and have a road record of 35-25. This is the series opener of a 3-game series with the Pirates on Friday. Their offense ranks 15th in the MLB with a .721 OPS. Payton Tolle was their starting pitcher on Thursday while Jake Bennett is making his start in this game on Friday. He is 7-5 with a 3.17 ERA this season. His team lost 2 of their last 3 games this season with him making an appearance. In his last MLB regular season appearance, he allowed 4 ER, 0 HR, and 3 BB with 5 SO on 5 hits through 5.1 IP against the Athletics.

The Pirates are entering this series off a win and lost their 3-game series against the Miami Marlins 2-1 in their last series. They enter this game with a 59-64 record overall and have a home record of 30-30. This is the 1st game of a 3-game series with the Red Sox on Friday. Their offense ranks 5th in the MLB with a .742 OPS. Braxton Ashcraft was their starting pitcher on Thursday while Bubba Chandler is making his start in this game on Friday. He is 5-8 with a 4.26 ERA this season. His team won their last 2 straight games this season with him making an appearance. In his last MLB regular season start, he allowed 0 earned runs, 0 homers, and 1 walk with 5 strikeouts on 3 hits through 6 innings pitched against the New York Mets.

The current betting odds have the Red Sox listed as a favorite in this game according to Draftkings Sportsbook. The Red Sox have looked really good in their games this season with their 64-56 record overall which has them right in the middle of the AL East. They have been a great road team too with their 35-25 road record this year. Meanwhile, the Pirates haven't looked great in their games this season with their 59-64 record overall which has them right at the bottom of the NL Central. They haven't looked great in their own ballpark either with their 30-30 home record this season. The Red Sox haven't been at their best lately, now 5-5 in their last 10 games after going through a rough patch the last week, but they have still been one of the hottest teams in the league over the last 2 months. The Pirates have been in their own slump lately too, going 3-7 in their last 10 games and their offense not performing in these. Chandler is going to be on the mound for the Pirates in this one and he hasn't looked great this year. He is 5-8 with a 4.26 ERA and he has been really up and down this season. He is coming off a great start giving up no runs and the team has won 2 games in a row now with him starting, but that hasn't been a common theme for him all year. The Red Sox are going with Bennett in this one and he has looked good this season. He is 7-5 with a 3.17 ERA and will be looking to bounce back from a rare bad start. He gave up 4 earned runs in his last start and even the team has lost 2 of their last 3 games with him starting, but that hasn't been a common theme for him. The Red Sox are going to be desperate to get themselves back on track while the Pirates have been starting to falter as of late, sliding down in the Wild Card race, so look for the Red Sox to take advantage of this pitching matchup with the more reliable staff. The best way to place a bet here is on the Red Sox to win this game. 

Red Sox Pirates Prediction:  Our MLB Pick for Friday, August 14, 2026 (6:40 pm ET start time) is Red Sox 5 Pirates 3.

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Boston Red Sox: 121-105 (+20.2 units) on the moneyline in road games. 176-152 (+4.8 units) on the moneyline against right-handed starters. 29-19 (+5 units) on the moneyline vs. NL teams allowing 4.5 or more runs/game on the season. 33-20 UNDER when playing against a team with a losing record.

Pittsburgh Pirates: 206-240 (-27.2 units) on the moneyline in all games. 114-109 (-5.2 units) on the moneyline in home games. 104-113 (-10.1 units) on the moneyline when the money line is +125 to -125. 22-16 UNDER against AL East opponents.

Boston Red Sox:  G. Whitlock (RP) Day To Day - Elbow. I. Kiner-Falefa (2B) Sixty Day IL - Forearm. C. Mead (3B) Ten Day IL - Hand. Z. Kelly (RP) Sixty Day IL - Elbow. R. Anthony (LF) Sixty Day IL - Wrist. G. Crochet (SP) Sixty Day IL - Shoulder. T. Story (SS) Sixty Day IL - Abdomen. K. Crawford (SP) Sixty Day IL - Wrist. T. Casas (1B) Sixty Day IL - Knee. J. Oviedo (SP) Sixty Day IL - Elbow. T. Houck (SP) Sixty Day IL - Elbow.

Pittsburgh Pirates:  E. Rodriguez (C) Day To Day - Hip. M. Keller (SP) Sixty Day IL - Arm. R. O'Hearn (RF) Ten Day IL - Quad. O. Cruz (CF) Sixty Day IL - Hand. K. Griffin (SS) Sixty Day IL - Finger.

“We got a big swing from Willson, that was good to see. If we can get him going, that turns things. We grinded, the pitching performances on both sides were good.” - Chad Tracy after his team’s loss against the Blue Jays in their game on Wednesday. 

“We have to compete. [Wednesday] was not good enough. I felt like we felt sorry for ourselves and didn't compete with the fight that we have all season, and we have to be better. We have to find a way, and we have to dig deep in the clubhouse — players, staff, everybody — and find a way." - Don Kelly after his team’s loss against the Marlins in their game on Wednesday. 

Masataka Yoshida (L) DH

Ceddanne Rafaela (R) CF

Adley Rutschman (S) C

Willson Contreras (R) 1B

Wilyer Abreu (L) RF

Caleb Durbin (R) 3B

Jarren Duran (L) LF

Andruw Monasterio (R) SS

Nick Sogard (S) 2B

Spencer Horwitz (L) 1B

Brandon Lowe (L) DH

Bryan Reynolds (S) LF

Nick Gonzales (R) 2B

Esmerlyn Valdez (R) RF

Jacob Gonzalez (L) SS

Jake Mangum (S) CF

Jared Triolo (R) 3B

Rafael Flores Jr. (R) C

Batting Average:  Jake Rogers (.500)

Hits:  Ceddanne Rafaela (130)

Home Runs:  Willson Contreras (24)

RBI:  Willson Contreras (71)

Stolen Bases:  Jarren Duran (17)

Wins:  Sonny Gray (14)

Saves:  Aroldis Chapman (27)

ERA:  Erik Miller (0.00)

Batting Average:  Ronny Simon (.333)

Hits:  Nick Gonzales (136)

Home Runs:  Brandon Lowe (25)

RBI:  Brandon Lowe (74)

Stolen Bases:  Oneil Cruz (21)

Wins:  Braxton Ashcraft (11)

Saves:  Gregory Soto (14)

ERA:  Khristian Curtis (0.00)

Managers:

Boston Red Sox: Chad Tracy (Interim)

Pittsburgh Pirates: Don Kelly (2nd season)