Alexei Popyrin upset fourth-seeded Daniil Medvedev at the Paris Masters to continue his fine year on the ATP Tour, securing his third career win over a top five opponent.
Popyrin, who improved to 26-21 for 2024 with his latest win, emerged a 6-4 2-6 7-6 (7-4) victor in just under two-and-a-half hours in the French capital.
The Australian, however, started poorly in the first set, with Medvedev earning an early break in the third game, only for Popyrin to claim the next three in a row.
Popyrin then missed four chances to close out the eighth game, but held his nerve to take the opener despite some late pressure from his Russian opponent.
But Medvedev responded emphatically in the second, managing back-to-back break points before taking the enthralling encounter to a decider.
The pair continued to trade blows in the third set and could not be separated, with a tie-break deciding who would face either Giovanni Mpetshi Perricard or Karen Khachanov in the last 16.
Popyrin let slip a 4-1 lead in the deciding set, but held his nerve to deal Medvedev his third consecutive opening round loss in Paris.
Data Debrief: Popping in Paris
Popyrin finally got the better of Medvedev, having lost his previous three matches against him at Wimbledon in 2019, the Australian Open in 2020 and the Miami Open in 2021.
In defeating Medvedev, Popyrin is the second Australian after Mark Philippoussis to register multiple wins against a top-five player at the Paris Masters.
The Australian had previously beaten Stefanos Tsitsipas in 2021, who was ranked as the world number three.
Zverev progresses to Paris Masters last 16 after seeing off Griekspoor
Alexander Zverev progressed to the last 16 of the Paris Masters following a straight-sets victory over Tallon Griekspoor.
The Italian Open champion prevailed 7-6 (7-2) 6-3 after just over an hour-and-a-half at Accor Arena.
The opening set remained on serve and went to a tie-break, which Zverev subsequently dominated to draw first blood.
Runner-up to Daniil Medvedev in this ATP Masters event four years ago, the German crucially claimed the match's only break in game six of the second set.
Zverev then subsequently held out for victory to set up a last-16 clash with Arthur Fils, who defeated him in the Hamburg final earlier this season.
Data Debrief: Zverev gets his break
Zverev maintained his perfect record against Griekspoor in 2024, having now won all four of their meetings, but it was a contest of fine margins.
Indeed, Griekspoor was dominant on serve early on, losing just one of his opening 14 points. However, the only break point he faced was ruthlessly pounced upon by the German, who saved all three he faced.
Unforced errors were also crucial with Zverev committing just nine to his opponent's 17, and his quest for a second trophy of the season continues.
Ruud crashes out of Paris Masters after Thompson defeat
Casper Ruud suffered an early exit at the Paris Masters, after he was beaten in three sets by Jordan Thompson.
The three-time major finalist was the latest big name to fall at the Accor Arena, where his Australian opponent prevailed 7-6 (7-3) 3-6 6-4.
Ruud took early control of the contest, breaking in game four to move to the brink of drawing first blood at 5-2 up.
However, Thompson broke back and then controlled the tie-break to edge his nose ahead.
Ruud - a two-time French Open runner-up in Paris - responded by breaking twice in the second set to level.
The two players exchanged breaks early in the decider, which looked set to go the distance until a timely break to love in game nine proved crucial for Thompson, who then held to set up a last-16 clash with either Zizou Bergs or Adrian Mannarino.
Data Debrief: Ruud's rueful form continues
A winner in Barcelona and Geneva earlier in the season, Ruud has been unable to maintain that momentum.
The Norwegian, who occupies sixth place in the Race to Turin, has now lost seven of the last eight matches he has played, and now requires favours from elsewhere to secure his place in the Nitto ATP Finals.
Nevertheless, Thompson deserves credit for taking his chances when they arrived. In fact, the Australian converted three of the four break-point opportunities that were presented to him.
Rublev's ATP Finals hopes dented after early Paris Masters exit
Andrey Rublev's Nitto ATP Finals hopes were dented after suffering a first-round exit against Francisco Cerundolo at the Paris Masters.
Rublev, who currently occupies eighth place in the Race to Turin, cut a frustrated figure as he was beaten 7-6 (8-6) 7-6 (7-5) by his Argentine opponent.
A semi-finalist at the indoor ATP Masters event 12 months ago, the sixth seed broke early for a commanding 5-2 lead in the opening set.
However, Cerundolo came roaring back, breaking twice for a 6-5 advantage, before drawing first blood in the tie-break.
Once again, Rublev was in control of the second set, with his second break putting him 4-2 to the good.
But Cerundolo hit back once more, breaking in game eight and then prevailing again in the tie-break for the 100th ATP win of his career.
His reward is a showdown with Stefanos Tsitsipas, who beat Alejandro Tabilo 6-3 6-4.
Data Debrief: Rublev's ATP Finals fate in the air
It took two hours and 18 minutes, but it was worth the wait for Cerundolo, who won his fourth match in seven against a top-10 opponent in 2024.
The Argentine struck 35 winners, while winning 86% (six out of seven) of points at the net.
As for Rublev, whose frustration culminated in him lashing the racquet against his knee, he must now nervously await his ATP Finals fate.
Tsitsipas, Alex de Minaur and Grigor Dimitrov are among the players in action this week who could deny the Madrid Open champion his fifth successive appearance at the year-end championship.
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