Pittsburgh Pirates vs Chicago Cubs Prediction & Picks - MLB

USA - MLB

Pittsburgh Pirates
5/25/26 13:35
Chicago Cubs

Prediction:

 

The Pirates will win

+105
$250 offered for betting!

New customers only | Commercial content | 21+ age limit | T&Cs apply

 by Lou Aguila | in MLB Picks

The Pittsburgh Pirates appear poised to pull off an upset with Carmen Mlodzinski looking to sustain his dominance against the Chicago Cubs on Monday.

The Chicago Cubs suffered their 8th consecutive loss after falling to the Houston Astros 5-8 in the series finale on Sunday. The Cubs found themselves on the receiving end of a sweep at the hands of the Astros and Brewers while losing two out of three games against the White Sox. As a result, the Cubs dropped to third in the NL Central with a 29-24 record, 2.5 games behind the new division leaders, the 30-20 Brewers.

The Pittsburgh Pirates prevented a sweep as they gutted out a 4-1 win over the Toronto Blue Jays in the series finale. The Pirates have won three of their last five games, bumping their record above .500 at 27-26.

Caesars Sportsbook lists the Chicago Cubs as the favorites (-125) for the series opener, heavily influenced by a 7-3 record over the Pirates in their last 10 meetings.

Meanwhile, the Pirates command a +105 on the moneyline and -170 to cover +1.5 runs.

The Sportsbooks set the over/under at 8.0 runs, even though two strong starters are scheduled to go head-to-head on Monday.

Fresh off a shutout stint against the Cardinals, Pirates’ RHP Carmen Mlodzinski (4-3, 3.96 ERA) will duke it out against Cubs’ RHP Ben Brown (1-2, 2.09 ERA).

Up to $250 to bet on Pittsburgh Pirates - Chicago Cubs! 

Limited Offer. Currently at Caesars Sportsbook

Pittsburgh Pirates vs Chicago Cubs Form

Table

Teams Pts P W L
7 Chicago Cubs
0.542 83 45 38
16 Pittsburgh Pirates
0.494 83 41 42

Pittsburgh Pirates and Chicago Cubs Latest Matches

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

3/6 (50%)

Defeats

3/6 (50%)

May 24, 2026 - MLB

Toronto Blue Jays
1 :  4
Pittsburgh Pirates

May 23, 2026 - MLB

Toronto Blue Jays
5 :  2
Pittsburgh Pirates

May 22, 2026 - MLB

Toronto Blue Jays
6 :  2
Pittsburgh Pirates

May 21, 2026 - MLB

St. Louis Cardinals
2 :  6
Pittsburgh Pirates

May 20, 2026 - MLB

St. Louis Cardinals
0 :  7
Pittsburgh Pirates

May 19, 2026 - MLB

St. Louis Cardinals
9 :  6
Pittsburgh Pirates
W L W L L L
Victories

2/6 (33%)

Defeats

4/6 (67%)

May 17, 2026 - MLB

Pittsburgh Pirates
0 :  6
Philadelphia Phillies

May 16, 2026 - MLB

Pittsburgh Pirates
0 :  6
Philadelphia Phillies

May 15, 2026 - MLB

Pittsburgh Pirates
9 :  11
Philadelphia Phillies

May 14, 2026 - MLB

Pittsburgh Pirates
7 :  2
Colorado Rockies

May 13, 2026 - MLB

Pittsburgh Pirates
4 :  10
Colorado Rockies

May 12, 2026 - MLB

Pittsburgh Pirates
3 :  1
Colorado Rockies
L W W L L W
Victories

3/6 (50%)

Defeats

3/6 (50%)

May 24, 2026 - MLB

Toronto Blue Jays
1 :  4
Pittsburgh Pirates

May 23, 2026 - MLB

Toronto Blue Jays
5 :  2
Pittsburgh Pirates

May 22, 2026 - MLB

Toronto Blue Jays
6 :  2
Pittsburgh Pirates

May 21, 2026 - MLB

St. Louis Cardinals
2 :  6
Pittsburgh Pirates

May 20, 2026 - MLB

St. Louis Cardinals
0 :  7
Pittsburgh Pirates

May 19, 2026 - MLB

St. Louis Cardinals
9 :  6
Pittsburgh Pirates
Chicago Cubs
Chicago Cubs Latest matches
L L L L L L
Victories

0/6 (0%)

Defeats

6/6 (100%)

May 24, 2026 - MLB

Chicago Cubs
5 :  8
Houston Astros

May 23, 2026 - MLB

Chicago Cubs
0 :  3
Houston Astros

May 22, 2026 - MLB

Chicago Cubs
2 :  4
Houston Astros

May 20, 2026 - MLB

Chicago Cubs
0 :  5
Milwaukee Brewers

May 19, 2026 - MLB

Chicago Cubs
2 :  5
Milwaukee Brewers

May 18, 2026 - MLB

Chicago Cubs
3 :  9
Milwaukee Brewers
L L L L L L
Victories

0/6 (0%)

Defeats

6/6 (100%)

May 24, 2026 - MLB

Chicago Cubs
5 :  8
Houston Astros

May 23, 2026 - MLB

Chicago Cubs
0 :  3
Houston Astros

May 22, 2026 - MLB

Chicago Cubs
2 :  4
Houston Astros

May 20, 2026 - MLB

Chicago Cubs
0 :  5
Milwaukee Brewers

May 19, 2026 - MLB

Chicago Cubs
2 :  5
Milwaukee Brewers

May 18, 2026 - MLB

Chicago Cubs
3 :  9
Milwaukee Brewers
L L W W L L
Victories

2/6 (33%)

Defeats

4/6 (67%)

May 17, 2026 - MLB

Chicago White Sox
9 :  8
Chicago Cubs

May 16, 2026 - MLB

Chicago White Sox
8 :  3
Chicago Cubs

May 15, 2026 - MLB

Chicago White Sox
5 :  10
Chicago Cubs

May 14, 2026 - MLB

Atlanta Braves
0 :  2
Chicago Cubs

May 13, 2026 - MLB

Atlanta Braves
4 :  1
Chicago Cubs

May 12, 2026 - MLB

Atlanta Braves
5 :  2
Chicago Cubs

Pittsburgh Pirates against Chicago Cubs : Head to Head (H2H)

Pittsburgh Pirates

33 %

Chicago Cubs

67 %

Apr 12, 2026 - MLB

Chicago Cubs
7 :  6
Pittsburgh Pirates

Apr 11, 2026 - MLB

Chicago Cubs
3 :  4
Pittsburgh Pirates

Apr 10, 2026 - MLB

Chicago Cubs
0 :  2
Pittsburgh Pirates

Sep 17, 2025 - MLB

Pittsburgh Pirates
4 :  8
Chicago Cubs

Sep 16, 2025 - MLB

Pittsburgh Pirates
1 :  4
Chicago Cubs

Sep 15, 2025 - MLB

Pittsburgh Pirates
0 :  4
Chicago Cubs

Pittsburgh Pirates - Chicago Cubs Key Points

  1. Pittsburgh is 3-6 SU in its last 9 games.
  2. Pittsburgh is 1-4 SU in its last 5 games at home.
  3. Chicago Cubs is 0-8 SU in its last 8 games.
  4. Chicago Cubs is 2-6 SU in its last 8 games on the road.
Up to $250 to bet on Pittsburgh Pirates - Chicago Cubs! 

Limited Offer. Currently at Caesars Sportsbook

Our Pittsburgh Pirates vs Chicago Cubs Prediction

Fearless Forecast: The Pirates take the opener 4-1

Aside from its tempting +105 price, Pittsburgh appears to be in a strong position to win this series opener because of Carmen Mlodzinski’s pitching dominance against the Cubs.

Mlodzinski has surrendered only two earned runs over 13.1 innings across three starts against the Cubs. He also blanked the Cubs in his last two starts, including an April 10 stint where he pitched for 5.1 scoreless innings to power the Pirates to a 2-0 win.

Ben Brown is also a terrific starter with a 2.09 ERA this season, but with the way the Cubs are performing on both sides of the ball, he must deliver a near-flawless performance or else his team has no chance of winning this ballgame.

Over the last five games, the Cubs’ starters have registered a 6.31 ERA over the last five games. Offense has also gone south as they average 1.8 runs on a .153 during this five-game stretch.

Our betting prediction for the Chicago Cubs vs the Pittsburgh Pirates: The Pirates will win.

Prediction:

 

The Pirates will win

+105
$250 offered for betting!

Caesars Rewards Program

Caesars Rewards

Caesars Sportsbook really spoils new users with an awesome rewards program, making every wager count towards something bigger! Available for users across the country, this program is a bettor's dream. As you enjoy the thrills of sports betting or casino games online, you can earn up to 10 Reward Credits for every $100 wagered on straight bets. And if parlays are more your style, you'll earn up to 20 Reward Credits for every $100 wagered. With Caesars Sportsbook, your bets not only bring the excitement of the game but also the joy of accumulating rewards that enhance your gaming experience. Play now and let Caesars treat you like royalty with each bet you place!

Sign-up now!

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

Pittsburgh Pirates vs Chicago Cubs Picks