Nick Kyrgios’s win over Rafael Nadal will go down as one of the greatest shocks ever at Wimbledon.

The 144-ranked kid from Canberra took the game to the world’s top player and tournament second seed, with a near-perfect serving game in three gruelling sets, before clinching the crucial break to claim the fourth and a place in Australian tennis history.

But where does Kyrgios’s win rank in the greatest shocks in the world’s top grass-court tournament? Here are five of the biggest upsets from the memory vault.

Nadal booted out by Lukas Rosol

Rosol wins 6-7 (11/9), 6-4, 6-4, 2-6, 6-4 (second round, 2012)

Nadal is no stranger to the odd shock result, but his early exit in 2012 came as a big upset when matched against Czech player Lukas Rusol.

Having just won his customary French Open title for the year, Nadal conspired to lose in a five-set heartbreaker, with the final set seeing Rosol win an arm wrestle despite Nadal only conceding 16 unforced errors.

It was Nadal’s earliest grand slam loss since 2005, although he again bowed out early in 2013 to Steve Darcis (ranked 135 in the world) in an injury-blighted year.

Jelena Dokic beats world number one Hingis

Dokic wins 6-2, 6-0 (first round, 1999)

A young Jelena Dokic – ranked 129th in the world – ripped through an emotionally shattered Martina Hingis, fresh after a French Open final collapse against Steffi Graf.

Hingis had earlier won the Australian Open that year, but was powerless to stop the up-and-coming Australian teen from powering past in the first set, before sensationally delivering a bagel in the second and final set.

Hingis would never again go on to win a grand slam tournament.

Peter Doohan shocks Boris Becker

Doohan wins 7-6, 4-6, 6-2, 6-4 (second round, 1987)

Still considered one of Wimbledon’s greatest upsets of all time, the on-fire Boris Becker – who had won the tournament as an unseeded 17-year-old in 1985 – came up well short against Australia’s Peter Doohan.

The unheralded Doohan took four sets to oust the 19-year-old Becker from the second round, with the top seed yet to drop a match in his fledgling Wimbledon career.

In contrast, Doohan had yet to win a match at the All England Club in four previous attempts.

Doohan brought out the perfect match to blast past the German, who would go on to win two more grand slam titles on grass.

Curren too good for McEnroe

Curren wins 6-2, 6-2, 6-4 (quarter-finals, 1985)

John McEnroe was expected to demolish all before him en route to another grand slam title after beating all comers in 1984, a year in which he compiled an incredible 82-3 win-loss record.

But the defending champion at Wimbledon had no answer to the big-serving South African Kevin Curren in 1985.

The straight-sets loss to Curren was McEnroe’s worst loss since becoming the world’s number one player, and marked the end of his grand slam title runs, never winning a major prize for the remainder of his career.

Ageing Sampras goes down to Bastl

Bastl wins 6-3, 6-2, 4-6, 3-6, 6-4 (second round, 2002)

In a day that saw Andre Agassi bow out to Marat Safin, Pete Sampras added to the top seeds scrapheap with a shock loss to Swiss world number 145 George Bastl.

Sampras had already made complaints about not playing on a showcourt, and Bastl pounced on the American’s irritations with a five-set triumph on court number two.

But the year would provide a happier memory for Sampras as he went on to secure a then-record 14th grand slam title, beating Andre Agassi in the US Open final before retiring.