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Alex de Minaur pulled off the biggest upset so far at the Rolex Paris Masters on Wednesday, rallying from 2-0 down in the third set—and fighting off a break point serving at 4-all in the decider—to take out Daniil Medvedev, 6-4, 2-6, 7-5.

And with the victory, the 23-year-old Australian achieves a big milestone: De Minaur’s win over the No. 3-ranked Medvedev was the first Top 5 win of his career, having been 0-18 against the elite going into the match.

De Minaur had six career wins over Top 10 players before this, three against No. 7s (Kei Nishikori at the 2019 US Open, Alexander Zverev at the 2020 ATP Cup and Matteo Berrettini at the 2022 ATP Cup) and three against No. 10s (Roberto Bautista Agut at 2019 Zhuhai, Bautista Agut again at 2019 Paris, Cameron Norrie at 2022 Barcelona).

But he had never sealed the deal against a Top 5 player before, despite coming close several times, including in his very first encounter with a member of the elite—he led a No. 5-ranked Zverev two sets to one in Davis Cup action in 2018 before falling in a fifth set tie-break after just under four hours.

DE MINAUR VS TOP 5 PLAYERS:
l. to No. 5 Zverev in 2018 Davis Cup, 7-5, 4-6, 4-6, 6-3, 7-6 (4)
l. to No. 1 Nadal in 2018 Wimbledon 3rd Rd, 6-1, 6-2, 6-4
l. to No. 3 Zverev in 2018 Washington D.C. F, 6-2, 6-4
l. to No. 5 Zverev in 2018 Shanghai 3rd Rd, 6-1, 6-4
l. to No. 2 Nadal in 2019 Australian Open 3rd Rd, 6-1, 6-2, 6-4
l. to No. 3 Zverev in 2019 Acapulco QFs, 6-4, 6-4
l. to No. 3 Federer in 2019 Basel F, 6-2, 6-2
l. to No. 1 Nadal in 2020 ATP Cup, 4-6, 7-5, 6-1
l. to No. 3 Thiem in 2020 US Open QFs, 6-1, 6-2, 6-4
l. to No. 5 Medvedev in 2020 Paris 3rd Rd, 5-7, 6-2, 6-2
l. to No. 5 Tsitsipas in 2021 Barcelona 3rd Rd, 7-5, 6-3
l. to No. 4 Thiem in 2021 Madrid 3rd Rd, 7-6 (7), 6-4
l. to No. 3 Tsitsipas in 2021 Indian Wells 4th Rd, 6-7 (3), 7-6 (3), 6-2
l. to No. 4 Zverev in 2021 Vienna 2nd Rd, 6-2, 3-6, 6-2
l. to No. 2 Medvedev in 2022 ATP Cup, 6-4, 6-2
l. to No. 4 Tsitsipas in 2022 Rotterdam QFs, 6-4, 6-4
l. to No. 5 Tsitsipas in 2022 Miami 3rd Rd, 6-4, 6-3
l. to No. 3 Zverev in 2022 Rome 3rd Rd, 6-3, 7-6 (5)
d. No. 3 Medvedev in 2022 Paris 2nd Rd, 6-4, 2-6, 7-5

Awaiting De Minaur in the third round in Paris will be Frances Tiafoe. The Australian has won both of his previous tour-level meetings against the American.