Boston Red Sox vs Pittsburgh Pirates Picks and Prediction for Sunday, August 16, 2026

By: David Anicetti Published 08/16/2026, 06:00 AM ET

The Boston Red Sox visit the Pittsburgh Pirates on Sunday at 1:35 PM ET at PNC Park. Boston is 65-57, third in the AL East and 9.5 games behind Tampa Bay after Friday’s 8-4 loss to Pittsburgh. The Red Sox are 1-4 over their last five games and 36-26 on the road. Pittsburgh is 60-64, fifth in the NL Central and 15.5 games behind Milwaukee after Friday’s win. The Pirates are 2-3 over their last five and 31-30 at home. Pittsburgh leads the series 1-0 entering Saturday’s matchup. Here is our betting breakdown and our free MLB picks.

Boston Red Sox Look to Patrick Sandoval

Boston is batting .248 with a .321 on-base percentage and .400 slugging percentage while scoring 542 runs with 122 home runs. Ceddanne Rafaela leads the Red Sox with a .288 average and 132 hits, while Willson Contreras has a team-high 24 home runs and 72 RBIs. Boston has struggled recently, scoring 19 runs while losing four of its last five games.

The Red Sox have been much stronger on the mound, ranking third in MLB with a 3.48 ERA and 1.22 WHIP. Patrick Sandoval starts Sunday with a 1-1 record, 3.30 ERA and 1.70 WHIP across 30 innings. The left-hander has 29 strikeouts against 13 walks while allowing 38 hits and three home runs. Boston has allowed 21 runs over its last five games.

Pittsburgh Pirates Send Paul Skenes to the Mound

Pittsburgh is batting .256 with a .334 on-base percentage and .413 slugging percentage while scoring 625 runs. The Pirates have hit 151 home runs, led by Brandon Lowe with 26 homers and 77 RBIs. Nick Gonzales leads Pittsburgh with a .307 average and 137 hits, though he is listed as day-to-day. The Pirates have scored 24 runs across their last two games after producing only three over the previous three.

Get Free $30 Credit for Premium Picks + Exclusive Discounts

Subscribe Now

I understand that I can unsubscribe at any time. I have read and accepted the Terms & Conditions and Privacy Policy. I consent that Winners and Whiners may use third-party services to process my data.

Pittsburgh ranks 22nd in MLB pitching with a 4.32 ERA and 1.32 WHIP, but Paul Skenes gives the Pirates a stronger matchup Sunday. Skenes is 9-11 with a 3.88 ERA and 1.12 WHIP over 134.2 innings. He has recorded 166 strikeouts against 37 walks while allowing 114 hits and 14 home runs.

Pitching Matchup

Boston Red Sox – Patrick Sandoval

Sandoval is 1-1 with a 3.30 ERA and 1.70 WHIP across 30 innings. The left-hander has allowed 38 hits, 13 walks and three home runs while striking out 29. Sandoval faces a Pittsburgh lineup batting .256 with a .334 on-base percentage and .413 slugging percentage. The Pirates have also scored 21 runs across their last two games, so Sandoval will need to reduce the traffic after allowing 51 combined hits and walks in his limited workload.

Pittsburgh Pirates – Paul Skenes

Skenes is 9-11 with a 3.88 ERA and 1.12 WHIP through 134.2 innings. The right-hander has allowed 114 hits, 37 walks and 14 home runs while recording 166 strikeouts. Skenes faces a Boston lineup batting .248 with a .321 on-base percentage and 122 home runs. His ability to miss bats and limit baserunners gives Pittsburgh an advantage against a Red Sox offense that has scored four runs or fewer in four of its last five games.

Boston Red Sox vs Pittsburgh Pirates Game Pick

  • Pittsburgh Pirates

Pittsburgh is the game pick behind Skenes. His 1.12 WHIP is well below Sandoval’s 1.70, and Skenes has struck out 166 hitters in 134.2 innings. The Pirates also hold the stronger offensive numbers with a .256 average, 625 runs, and 151 home runs. Pittsburgh scored eight runs against Boston on Friday and has produced 21 runs over its last two games. Pittsburgh is the play.

Boston Red Sox vs Pittsburgh Pirates Over/Under Pick

  • Under

The under is the total pick because Skenes can control Boston’s lineup, while the Red Sox bring one of MLB’s better pitching staffs into the matchup. Boston owns a 3.48 team ERA and has scored four runs or fewer in four of its last five games. With Skenes carrying a 1.12 WHIP and Boston ranking third in team pitching, Sunday’s matchup will cash under the closing total.

If you or someone you know has a gambling problem, crisis counseling and referral services can be accessed by calling 1-800-GAMBLER (1-800-426-2537) (IL). Gambling problem? Call 1-800-GAMBLER (MI/NJ/PA/WV/WY), 1-800-9-WITH-IT (IN), 1-800-522-4700 (CO), 1-800-BETS OFF (IA), 1-888-532-3500 (VA), 1-800-NEXT STEP (AZ), or call/text TN REDLINE 1-800-889-9789 (TN). 21+ (18+ WY). AZ/CO/IL/IN/IA/MI/NJ/PA/TN/VA/WV/WY only. Eligibility restrictions apply. T&C's Apply. Void where prohibited. If you click on a link on this site which takes you to a bookmaker or casino and you subsequently open an account, Pick and Parlays may receive a commission. Bets placed are the responsibility of the bettor.

Copyright © 2026 Picks and Parlays. All rights reserved.

The sports news and information contained at this site is for entertainment purposes only. Any use of this information in violation of laws whether they are federal, state and/or local is prohibited. Picks and Parlays is the nation's premier resource for sports betting and handicapping information.

Sign Up Get $30 Premium Picks Credit + Exclusive Offers
Special Offer
Up To $1500 in Bonus Bets Paid Back if your First Bet Does Not Win
Play now Gambling problem? Call 1-800-GAMBLER or 1-800-MY-RESET (Available in the US) 877-8-HOPENY or text HOPENY (467369) (NY) 1-800-327-5050 (MA), 1-800-BETS-OFF (IA), 1-800-981-0023 (PR). 21+ only. Please Gamble Responsibly. See BetMGM.com for Terms. First Bet Offer for new customers only (if applicable). Subject to eligibility requirements. Bonus bets are non-withdrawable. In partnership with Kansas Crossing Casino and Hotel. Promotional offers not available in Mississippi, New York, Ontario, or Puerto Rico.