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For me, I go with a top 300 ranked Daniel Nestor defeating then no.1 Stefan Edberg in 1992 I think in Davis Cup.

Other examples?
 

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Gasquet wasn`t in TOP-100 when he won his first match against Roger seven years ago. That was impressive.
 

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Olivietti vs Fish was pretty good this week.

Not sure what Nadal's ranking was when he beat Albert Costa, reigning French Open champion, at Monte Carlo, but don't think he was top 100 - that was impressive because of the venue & surface.

And of course Bastl beating Sampras at Wimbledon - that was sad. Especially being out on court 2. :sad: Can't imagine Wimbledon ever putting Roger or Rafa out there - the guy was a 7 time champion there - still can't believe they couldn't give him court. 1 at least...
 

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Safin coming out of nowhere to beat Guga and Agassi in Roland Garros. Federer beating Moya. Nadal beating Federer. Berdych beating Federer in the Olympics. I think Berdbrain was impressive because he had only played five ATP matches then.
 

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karlovic vs number 1 and defending champion L. Hewitt in Wimbledon 2003.
 

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#2 Rafael Nadal losing to #690 Joachim Johansson in Stockholm 2006.
 

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Tank and Bank from Rafa?

Just kidding, Pim Pim was a USO semi finalist and a decent player who got bogged down with injuries.
 

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Federer beating then world nr. 5 Carlos Moya as a 17-year old just inside Top 300 (I think) in Marseille in 1999.
 

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S-Hertogenbosch 2007 QF : Wessels (488) def Robredo (7) 6-3, 6-3

I know some people don't count him as a "top player" but still, not often a player outside top 400 beat a top 10.
 

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Wimbledon 2000 R64 : Voltchkov (237) def Pioline (6) 6-3, 6-3, 2-6, 3-6, 6-4
The gap is less impressive but he made it in GS and he also managed to beat El Aynaoui (16) during this tournament to reach the SF ranked 237 !!

Thinking about Voltchkov made me think about Dewulff also and his run as qualifier at RG 1997 to SF, where he beated Corretja who was in the top 10 at the time, Norman and Meligeni.
 

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Young Lleyton Hewitt (16 y 10 m) won the singles title in Adelaide in 1998 to become the lowest-ranked (#550) winner in the history of the ATP tour. He beat Andre Agassi in the semis. Following the win his ranking climbed to #200 in the world.

Respectfully,
masterclass
 
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Wimbledon 2000 R64 : Voltchkov (237) def Pioline (6) 6-3, 6-3, 2-6, 3-6, 6-4
The gap is less impressive but he made it in GS and he also managed to beat El Aynaoui (16) during this tournament to reach the SF ranked 237 !!

Thinking about Voltchkov made me think about Dewulff also and his run as qualifier at RG 1997 to SF, where he beated Corretja who was in the top 10 at the time, Norman and Meligeni.
Both awesome runs (especially with the 'Vladiator' story - he watched Gladiator numerous times which inspired him to makes the SFs as a lowly-ranked qualifier, heroic stuff), and Dewulf reached the QF the following year as well, in epic Popp/Pironkova-esque fashion.
 

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Young Lleyton Hewitt (16 y 10 m) won the singles title in Adelaide in 1998 to become the lowest-ranked (#550) winner in the history of the ATP tour. He beat Andre Agassi in the semis. Following the win his ranking climbed to #200 in the world.

Respectfully,
masterclass
Yes and he ditched his planned doubles partner for the Australian Open juniors that year after the title: Roger Federer.
 
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