Cubs vs. Pirates Picks & Prediction

May 28, 2026
6:40 PM ML O/U SCORE
Cubs +162 0
Pirates -180 0
Premium Picks [7] �? Free Picks [4]

Cubs vs. Pirates Premium Pick Packages

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Cubs vs. Pirates Free Picks & Predictions

Black Widow

Game Details
May 28, 2026 in 7h
MLB | CHC vs PIT
Play on: OVER 7½ -105

1* Free Wiseguy Play on Cubs/Pirates over 7½ -105

*All picks are based on situations, trends, statistics and injuries among many other factors*

Pick Released on May 28 at 07:03 am View Archive

Joseph D'Amico

Game Details
May 28, 2026 in 7h
MLB | Cubs vs Pirates
Play on: Pirates -163 at betonline

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Pittsburgh Pirates.

Game 952.

3:40 PM PST/6:40 PM EST.

Very quietly, the National League Central division has become the most competitive in all of baseball. They are the only division in the Majors possessing five teams all with winning records. But unfortunately, someone has to lead the division, and someone has to dwell in the cellar. Battling it out for the poorest record in the Central is everyone but the Milwaukee Brewers. One game separates the St. Louis Cardinals, Chicago Cubs, Cincinnati Reds, and Pittsburgh Pirates. We all know Chicago was riding a 10-game slide until yesterday’s game three victory by a score of 10-4. Prior to that, the Cubs accounted for a combined 25 runs scored during that 10-game losing streak. That would be enough. But their pitching staff got steamrolled for over 65 runs during that span. Obviously, yesterday, both their lineup and their staff came up big. However, I think today’s going to be a tough road outing for the Cubs. This is a team that is just 12-15 on the road. They lose a little something when they travel, folks. I am well aware as I mentioned a moment ago, they came up big yesterday. But they still have problems with Pittsburgh as they have dropped four of the six meetings between these two division rivals thus far this season. Speaking of the Pirates, yesterday’s defeat ended their three-game hot streak. This is a team that is 15-14 at home, and on paper, scores more and allows less than their visiting opponent. So, this game is going to come down to pitching. Colin Rea and Paul Skenes are scheduled. The Chicago right-hander is 4-3 with a 4.83 ERA on the campaign. Over his career in 10 appearances, which includes eight starts against Pittsburgh, he is 3-3 with a 5.09 ERA. He is also winless on the road in 2026 campaign, going 0-2 with whopping ERA of 6.75. The Pirates right-hander is 6-4 with an ERA of 3.00 this season. In seven career starts against the Cubs, he is 2-2 with a 2.94 ERA, and at home in 2026, he has pitch quite well, going 3-2 with the 2.62 ERA. Skenes comes off his two worst appearances this season, and I expect him to bounce back here today in a big time. Prior to those last two outings, he had eight appearances, allowing a combined six earned runs. I feel he comes back to form here and pitches well, while his lineup takes care of the rest. Take the Pittsburgh Pirates. Thank you.

Pick Released on May 28 at 11:15 am View Archive

Brandon Lee

Game Details
May 28, 2026 in 7h
MLB | Cubs vs Pirates
Play on: Cubs +152 at Ace

Thursday's Free MLB Pick

PLAY ON: Cubs +152

Pick Released on May 28 at 08:30 am View Archive

Marc David

Game Details
May 28, 2026 in 7h
MLB | Cubs vs Pirates
Play on: Cubs +160 at Ace

Marc David Sports' Free Pick

We really like the underdog in this matchup. The Cubs halted a 10-game slide with a 10–4 win last night, and with Pittsburgh ace Paul Skenes  (6–4, 3.00 ERA) looking more hittable lately , nine runs on 15 hits allowed over 10 innings across his last two starts, we think Chicago can do some damage again.

This is a FREE PLAY on the CUBS!

Pick Released on May 28 at 06:40 am View Archive