Frenchman Arthur Gea failed to convert a match point that would have seen him make history as the first lucky loser to reach the quarter-finals of the US Open.

Instead, the 21-year-old fell in a gruelling five-set encounter with Botic van de Zandschulp, having also failed to serve out victory when he had the chance in the fourth set.

Three hours after holding match point, the world No 87 was out, with Van de Zandschulp battling back to win 3-6, 6-7 (0-7), 7-6 (9-7), 7-6 (7-3), 6-4 in five hours and 13 minutes — the fourth-longest match on record in New York.

Gea had to go through qualifying, as his ranking was not high enough to automatically qualify for the main draw when entry lists were published. He lost to Nishesh Basavareddy in the final round of qualifying but received a reprieve when former runner-up Casper Ruud withdrew with injury before the tournament began, taking the Norwegian’s place.

Netherlands’ Botic van de Zandschulp celebrates winning © IMAGN IMAGES via Reuters

Gea seized his opportunity by making the fourth round but could not get past world No 70 van de Zandschulp, although he may take some comfort in his prize money of $480,000 – more than seven times the $66,000 he had expected to earn through qualifying.

Van de Zandschulp now faces a race to recover in time from that epic encounter before he faces top seed Alexander Zverev.

Gea seized his opportunity by making the fourth round but could not get past world No 70 van de Zandschulp, although he may take some comfort in his prize money of $480,000 — more than seven times the $66,000 he had expected to earn through qualifying.

Van de Zandschulp now faces a race to recover in time from that epic encounter before he faces top seed Alexander Zverev.

The French Open champion made smooth progress against Luciano Darderi, beating the 21st seed 6-2, 6-2, 7-6(3) to reach the quarter-finals in a rare finish before midnight local time.

The top seed had made heavy weather of his first two matches in New York, grinding out five-set wins in nearly five hours in both, but has ticked off his next two in straight sets – although before beating Darderi each match had ended after 1.0am.

The other quarter-final in this half of the draw will see Russian world No 50 take on Belgian 28th seed Alexander Blockx, who nearly retired with a rib injury in his four-set win over 24th seed Francisco Cerundolo.

Khachanov, meanwhile, took five sets to dispatch American 14th seed Learner Tien, who was visibly emotional as he exited his home Grand Slam.