(Photo credit: Mike Frey-Imagn Images)

Croatian qualifier Dino Prizmic earned his first career top-10 win, toppling No. 4 seed Ben Shelton 6-4, 6-7 (4), 7-6 (5) in a marathon three-hour match to reach the third round of the Madrid Open on Friday.

Prizmic, 20, was excellent on his serve, winning 70.6% of his service points (77 of 109) and never facing a break point in the match. Shelton had twice as many aces (10-5) and more winners (44-31) but also more unforced errors (44-28).

Prizmic is through to the third round of an ATP Masters 1000 event for the first time.

'It means a lot,' Prizmic said after the win. 'Today was a very hard match for me and I just tried to play my game, stay focused every point and it definitely worked today. I'm working a lot with my team to stay calm on the important points, but (Shelton) is No. 6 in the world. ... I was waiting for my chances, and I took them in the end.'

Shelton saved 5 of 6 break points. The only break of the match, down 5-4 in the first set, proved to be the difference, snapping his five-match winning streak.

Prizmic wasn't the only player to secure his first career top-10 victory on Friday. Spanish wild card Rafael Jodar, playing in his hometown, coasted past No. 5 Alex de Minaur of Australia 6-3, 6-1 in 75 minutes.

Jodar, 19, won nearly as many of his return points (57.6%) as he did service points (61.2%), converting 6 of 13 break-point chances. de Minaur had just three winners and 26 unforced errors.

Jodar, who won his first ATP title earlier this month in Marrakech and then made the Barcelona semifinals, will face Brazilian 19-year-old Joao Fonseca, who advanced over Croatia's Marin Cilic via walkover, in a battle of the two youngest top-100 ranked players for a Round of 16 spot.

There was plenty of other Friday carnage with seeded competitors losing their opening matches. No. 9 Russian Andrey Rublev fell 6-3, 6-4 to Czech Vit Kopriva; No. 14 Valentin Vacherot of Monaco lost 6-7 (5), 7-6 (1), 6-3 to Emilio Nava; and No. 15 Tommy Paul was defeated by Argentina's Thiago Agustin Tirante 7-5, 6-4.

No. 32 Canadian Gabriel Diallo was forced to retire due to an injury against qualifier Elmer Moller of Denmark when down 7-5, 3-3.

World No. 1 Jannik Sinner nearly joined the ranks of the early exits, but rallied for a 6-7 (6), 6-1, 6-4 win over French qualifier Benjamin Bonzi to secure his 18th straight victory.

A number of seeded players took care of business. No. 6 Lorenzo Musetti of Italy swept Poland's Hubert Hurkacz 6-4, 7-6 (4). No. 22 Arthur Rinderknech of France blew past Serbian qualifier Dusan Lajovic 6-3, 6-2. No. 25 Tomas Martin Etcheverry of Argentina bested Austria's Sebastian Ofner 6-4, 6-4, and Dutch 29th seed Tallon Griekspoor held off Bosnia and Herzegovina's Damir Dzumhur 6-3, 6-4.

In three-set action, No. 11 Czech Jiri Lehecka rallied for a 3-6, 7-6 (3), 6-4 triumph over Chile's Alejandro Tabilo; No. 19 Brit Cameron Norrie outlasted Tomas Machac of the Czech Republic 6-2, 6-7 (6), 7-6 (5); and No. 21 Arthur Fils of France pulled off a 6-7 (4), 7-6 (3), 7-5 comeback victory over Peru's Ignacio Buse.

In the only matchup of the day between unseeded foes, Alex Michelsen routed Germany's Jan-Lennard Struff 6-2, 6-1 in 58 minutes.

--Field Level Media