Pirates vs. Yankees Prediction, Odds, Probable Pitchers, Prop Bets for Monday, July 20

The New York Yankees salvaged the back half of their doubleheader with the Los Angeles Dodgers on Sunday, moving them to 11 games over .500 and just 1.5 games out of the top spot in the AL East heading into Monday’s series against the Pittsburgh Pirates.

Pittsburgh (52-48) is in a three-way tie for the final wild card spot in the National League, and it has an impressive plus-54 run differential in the 2026 season. The Pirates rank first in the league in batting average, second in OPS, second in Weighted Runs Created Plus (wRC+) and second in runs scored, sporting one of the most dangerous attacks in the league.

Meanwhile, the Yankees have been slumping over the last month plus, as Aaron Judge, Giancarlo Stanton and several others have been sidelined.

New York is 6-4 in its last 10 games, but it is 9-16 over its last 25.

Ryan Weathers (4.15 ERA) will get the ball for New York in this series opener against Pirates right-hander Braxton Ashcraft.

Let’s dive into the odds, a player prop to bet and my prediction for the series opener between these two teams with playoff aspirations.

Pirates vs. Yankees Odds, Run Line and Total

Odds via DraftKings Sportsbook

Run Line

Pirates -1.5 (+163)
Yankees +1.5 (-199)

Moneyline

Pirates: -103
Yankees: -117

Total

7.5 (Over -119/Under -102)

Pirates vs. Yankees Probable Pitchers

Pittsburgh: Braxton Ashcraft (9-3, 3.49 ERA)
New York: Ryan Weathers (3-7, 4.15 ERA)

Pirates vs. Yankees How to Watch

Date: Monday, July 20
Time: 7:05 p.m. EST
Venue: Yankee Stadium
How to Watch (TV): YES Network, MLB.TV
Pirates record: 52-48
Yankees record: 55-44

Pirates vs. Yankees Best MLB Prop Bets

Yankees Best MLB Prop Bet

Braxton Ashcraft OVER 6.5 Strikeouts (-128)

SI Betting’s Iain MacMillan included Ashcraft in his daily column where he is betting $100 a day for an entire year. He believes this is a great spot for the Pirates right-hander to rack up the strikeouts:

The New York Yankees' offense has been horrible lately, and one of their biggest issues is striking out. Over the past 30 days, they have a strikeout rate of 28.3%, which is the most in the Majors in that time frame by a whopping 1.3%. That should set up well for Braxton Ashcraft, who has averaged 6.7 strikeouts per start since the beginning of June.

Pirates vs. Yankees Prediction and Pick

The Pirates have won seven of their last 10 games, and they are making a real case to be a playoff team in the National League.

Meanwhile, the Yankees have been sputtering for weeks and are only in the mix for the AL East lead thanks to a five-game losing streak by the Tampa Bay Rays.

New York has played under .500 baseball for over a month, and it has struggled with Weathers on the mound, going 8-10 in 18 starts. On top of that, the left-hander has a 5.35 ERA in seven outings since June 1, leading New York to a shaky 2-5 record during that stretch.

Ashcraft has been a much better pitcher, ranking in the 77th percentile in expected ERA (3.31) while leading Pittsburgh to a 13-6 record in 19 outings. The Pirates also have a thriving offense at the moment, making them a tough team to fade if they also have the pitching advantage.

I’ll take a shot on Pittsburgh getting an upset win on Monday night.

Pick: Pirates Moneyline (-103 at DraftKings)

Odds refresh periodically and are subject to change.

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