Taillon (3-6) limited the Yankees to just Gleyber Torres' single to center in the first and a pair of walks and outpitched Carlos Rodón in the All-Star's injury-delayed Yankees debut. Taillon struck out four, set his season high for innings and didn't allow a runner past first base in his first victory since June 13.
"Best Cub outing I think he's had," manager David Ross said. "The secondary stuff he was landing at will. The mix was just really good."
A 31-year-old right-hander, Taillon spent two seasons with the Yankees, then agreed in December to a $68 million, four-year contract with Chicago. In Friday's game, he became the first former Yankee to pitch eight or more innings and allow no more than one hit at Yankee Stadium old or new, according to Opta.
"I just needed an outing like this period," Taillon said. "I have a lot of love for those guys over there, so it's not like I wanted to stick it to them. This wasn't like any sort of revenge game or anything like that. ... But it does feel good on this stage in New York City to have a good night."
Meanwhile, Rodón (0-1), who is coming off consecutive All-Star seasons, threw predominantly fastballs (53) and sliders (12), mixing in two curveballs and a pair of changeups. He averaged 95.5 mph with his fastball but got just five misses among 30 swings.
"It was fun to watch him get after it," Yankees manager Aaron Boone said.
Rodón allowed two runs and four hits in 5⅓ innings with two walks and two strikeouts.
The 30-year-old lefty started his career with the White Sox, spent 2022 with San Francisco and signed a $162 million, six-year contract with the Yankees last winter. He strained his left forearm during spring training and was slowed by a bad back during rehab, causing him to miss the first half of the season.
"It's nice to finally pitch in the pinstripes in Yankee Stadium," Rodón said, "but not the way I wanted to start."
Cody Bellinger hit his ninth home run for the Cubs, who had been 0-12 at Yankee Stadium old and new. Chicago had lost eight regular-season games in the Bronx plus two each as the Yankees swept the 1932 and 1938 World Series.
New York lost its third straight, dropping to 13-16 since Aaron Judge tore a ligament in his right big toe on June 3. Booed repeatedly by angry fans, the Yankees have scored two runs or fewer in 12 of those games.
Adbert Alzolay gave up a ninth-inning single to Franchy Cordero and finished a two-hitter for his sixth save in seven chances. Chicago, which had dropped eight of its previous 11, tied Toronto for the big league lead with 10 shutouts. The Yankees were blanked for just the fourth time.
Bellinger drove a fastball high over the right-field wall in the third for Chicago's first hit. He took a half-dozen small steps as he watched the ball land in the second deck, giving him 20 hits in his past 40 at-bats.
Chicago got its second run in the fifth, when Rodón walked Trey Mancini and Miguel Amaya and Nico Hoerner grounded a two-out RBI single through the right side. Patrick Wisdom added an RBI double in the seventh against Ron Marinaccio.
The Associated Press contributed to this report.