Ben Shelton suffered a shock first-round exit at Wimbledon, as the fourth seed was beaten by qualifier Otto Virtanen in a five-set thriller.

Shelton, who had never lost his opening match at SW19, became the highest-profile casualty in the men's singles draw, after losing 6-4 3-6 6-7 (8-10) 6-2 7-6 (11-9) in a four-hour epic on No.2 Court.

Virtanen was aiming to become the first Finnish player to defeat a top-10 player at Wimbledon, and made an ideal start as he broke at the fourth attempt in game nine on the way to winning the opening set.

Shelton responded, and a single break was enough to help him level, before he came through a third-set tie-break to complete the turnaround.

A winner in Dallas, Munich and Stuttgart this season, Shelton could not build on that momentum, though, as Virtanen hit back with a pair of breaks in the fourth set to take the contest the distance.

The 25-year-old, seeking a first ATP-level win since last season in s'Hertogenbosch, survived a scare in the decider, rescuing break point in game eight on the way to forcing a tie-break.

Virtanen found himself 8-5 down, but roared back by winning five of the next six points to complete a shock victory.

Alex de Minaur recovered from a slow start before racing away from Wimbledon debutant Roman Andres Burruchaga.

The Australian – a winner of his past 16 opening matches at grand slams – found himself 3-0 down as he was broken at the start of the opening set.

However, after breaking back and overturning a 4-3 defeat to prevail in the tie-break, it was one-way traffic as De Minaur won 12 of the next 13 games.

The sixth seed, who broke in games four and six of the second set, won 10 of the last 11 points to go two up, and broke three times while dropping just a single point on serve in the final set to run out a 7-6 (7-5) 6-1 6-0 winner.

De Minaur's 67 match wins at majors is the second-most among players from outside Europe in the past decade – behind only Taylor Fritz (68), who beat Dusan Lajovic 6-3 6-4 6-3.

Zizou Bergs, meanwhile, completed his second victory over Ugo Humbert in the space of two days, as he beat the Frenchman 6-2 7-5 4-6 3-6 6-3.

Virtanen's victory for the ages

There is a Finn at the top of the ATP's doubles rankings, in the form of Harri Heliovaara, but Virtanen is ranked at 140 in the singles charts.

However, he became only the second Finn to beat a top-10 opponent in a grand slam, after Jarkko Nieminen beat Andre Agassi at the 2005 French Open.

It was a miserable day at the office for Shelton, who had won his past 12 opening men's singles matches at the majors and would have been hopeful of a deep run here, especially with no Carlos Alcaraz to contend with in the draw.

Shelton's compatriot Fritz at least ensured another big-name American did not suffer an early exit.

He hit 14 aces, won 83% of points on his first serve, and broke his opponent – a late replacement for the injured Jack Draper – four times to claim a 13th win in 15 opening main-draw matches at grand slam events.