It wasn’t easy—he was broken in both sets—but Grigor Dimitrov made a winning start to his Delray Beach campaign on Thursday night, beating American qualifier Mitchell Krueger, 7-6 (4), 6-3.

Not only did the victory put him through to the quarterfinals of the ATP 250 event, it also gave him a new milestone: it was the 350th tour-level win of Dimitrov’s career (350-232).

Even better: Dimitrov is just the second man born in the 1990s or later to reach 350 career tour-level wins, after another former No. 3, Milos Raonic, who has 372 career wins (372-175).

Dimitrov was born in 1991, while Raonic was born in 1990.

Kei Nishikori was just a few days from being on that short list, too—the 2014 US Open finalist, who has a 431-211 career win-loss record, was born on December 29th, 1989.

Dimitrov, a three-time Grand Slam semifinalist and 2017 ATP Finals champion, is the 130th man in the Open Era to reach 350 career wins, and the 22nd active player to do it after Roger Federer, Rafael Nadal, Novak Djokovic, Andy Murray, Richard Gasquet, Marin Cilic, Fernando Verdasco, Stan Wawrinka, Tommy Robredo, Gael Monfils, Feliciano Lopez, Gilles Simon, Philipp Kohlschreiber, Jo-Wilfried Tsonga, John Isner, Fabio Fognini, Andreas Seppi, Sam Querrey, Raonic, Ivo Karlovic and Kevin Anderson.