Pittsburgh Pirates vs Chicago Cubs Prediction & Picks - MLB

USA - MLB

Pittsburgh Pirates
5/27/26 18:40
Chicago Cubs

Prediction:

 

Pirates ML

-122
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 by Travis Pulver | in MLB Picks

The Pittsburgh Pirates (29-26, 15-13 Home) will go for the clean sweep of the Chicago Cubs today when they play at PNC Park in the Steel City. Fans can follow the action on MLB.TV once the game gets underway at 6:40 p.m. EST.

Pittsburgh has absolutely dominated the series so far, winning 2-1 on Monday and 12-1 in yesterday’s matchup.

Chicago will send Jameson Taillon to the mound to start the day. Taillon is 2-4 in ten starts with a 5.20 ERA and a 1.27 WHIP.  He struggled in his last outing, going just 4 2/3 innings against the Astros (May 22), allowing eight hits, one walk, and four earned runs while striking out five. It was his third loss in a row. Pittsburgh’s lineup has hit .269 against him in 108 at-bats (29 hits, four home runs).

Pittsburgh is scheduled to start Bubba Chanlder on the mound. The young righty is 1-6 in ten starts with a 4.79 ERA and a 1.47 WHIP. He faced the Cubs earlier in the season (April 12) in Chicago. He did not factor into the decision after pitching 5 1/3 innings and giving up five hits, two home runs, and three earned runs while striking out four and walking two.


 

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
W L L W W W
Victories

4/6 (67%)

Defeats

2/6 (33%)

May 26, 2026 - MLB

Pittsburgh Pirates
12 :  1
Chicago Cubs

May 25, 2026 - MLB

Pittsburgh Pirates
2 :  1
Chicago Cubs

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
W L L L W W
Victories

3/6 (50%)

Defeats

3/6 (50%)

May 26, 2026 - MLB

Pittsburgh Pirates
12 :  1
Chicago Cubs

May 25, 2026 - MLB

Pittsburgh Pirates
2 :  1
Chicago Cubs

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
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 26, 2026 - MLB

Pittsburgh Pirates
12 :  1
Chicago Cubs

May 25, 2026 - MLB

Pittsburgh Pirates
2 :  1
Chicago Cubs

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
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
W W L L L L
Victories

2/6 (33%)

Defeats

4/6 (67%)

May 26, 2026 - MLB

Pittsburgh Pirates
12 :  1
Chicago Cubs

May 25, 2026 - MLB

Pittsburgh Pirates
2 :  1
Chicago Cubs

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

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

Pittsburgh Pirates

67 %

Chicago Cubs

33 %

May 26, 2026 - MLB

Pittsburgh Pirates
12 :  1
Chicago Cubs

May 25, 2026 - MLB

Pittsburgh Pirates
2 :  1
Chicago Cubs

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

Pittsburgh Pirates - Chicago Cubs Key Points

  1. Pittsburgh leads the all-time series vs. the Cubs 1321-1288-17.
  2. The Cubs are 9-17 ATS (run line) on the road; the Pirates are 15-13 ATS (run line) at home.
  3. The OVER is 15-10-1 for the Cubs on the road and 17-11 for the Pirates at home.
  4. Public Betting: 63% of moneyline tickets and 49% of the handle are on the Pirates.

Our Pittsburgh Pirates vs Chicago Cubs Prediction

Neither pitcher in this outing is impressive, which tells me the winner will be whoever can generate some offense. With how both teams have been playing, it will probably not be the Cubs. Chicago has been struggling at the plate over the last week, hitting just .178 and scoring nine runs over the last five games. Now, this could be the game they break out of their slump in, but teams are hitting .206 against Chandler when he’s pitching at home. It’s not going to happen.

Our Chicago vs. Pittsburgh Pick: Pirates ML

Prediction:

 

Pirates ML

-122
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Pittsburgh Pirates vs Chicago Cubs Picks