Pittsburgh Pirates vs Chicago Cubs Prediction & Picks - MLB

Prediction published on 5/28/26, 3:14 PM  by Lou Aguila | Modified on 5/28/26 at 10:35 PM in MLB Picks

Betting on a rare Chicago Cubs back-to-back win over the Pittsburgh Pirates on Thursday could get you a handsome +143 payout.

The Pittsburgh Pirates’ three-game winning streak fell on Wednesday after finding themselves on the receiving end of a 4-10 blowout against the Chicago Cubs.

The Pirates still carry a winning record of 29-27, but remain last in a brutally competitive NL Central Division.

As for the Cubs, they have just snapped a 10-game losing streak. Chicago also scored at least 10 runs for the first time since their 10-5 win over the White Sox on May 15.

The Cubs sit in third in the NL Central Division with a 30-26 record, 4.5 games behind the current division leader, the 33-20 Milwaukee Brewers.

Matchup Analysis:

The Cubs might have a shot at a back-to-back win despite facing Pirates ace Paul Skenes in Game 2.

After batting .199 with 3.2 runs per game over the last 10 games, Chicago’s offense suddenly woke up as it exploded for 10 runs in the series opener.

Although consistency continues to be the pressing issue for the Cubs, the offensive eruption in Game 1 should prop up their confidence in their upcoming faceoff with Skenes, who has given up 9 earned runs over his last 10 innings on the mound.

Cubs starter Colin Rea has posted a 5.06 ERA over his last five starts, but has historically performed well against the Pirates. Rea has only allowed an average of 1.7 earned runs and 3.7 hits across his last three starts vs. Chicago.