There is one tennis player who can boast of ending his career with a winning record in head-to-head matches against Jannik Sinner. It’s not Novak Djokovic, nor is it Carlos Alcaraz, but rather Mikhail Kukushkin, a 38-year-old Kazakhstani by adoption, who bid farewell to professional tennis in Almaty after losing his final match to Stefanos Tsitsipas. His small personal record, however, will remain intact: he leads the South Tyrolean 1-0.
To find the only previous match between the two, we have to go back to September 16, 2019, when they faced off in the first round of the ATP 250 in St. Petersburg. Sinner had just turned 18 and had entered the draw thanks to a wild card. On the other side of the net was a much more experienced opponent, who managed to prevail 6-3, 7-6(4) in one hour and 39 minutes on indoor hard court.
Even in that match, however, the young Jannik had shown his potential. The Italian had earned three break points in the first game and another four in the seventh, but failed to convert any of them. In the second set, he also had the opportunity to force a third set, but Kukushkin managed to use his experience to close out the match. It was hard to imagine, at the time, that that victory would become a curious statistic to remember upon his retirement.
In an interview after retiring, the Kazakh player fondly recalled that match, acknowledging that he had immediately sensed something special in the future world No. 1: “I remember that match. Sinner was very young, but he was already playing exceptionally well. You could tell he had something special. I was particularly struck by his attitude: he was very aggressive, focused, and confident,” Kukushkin said.