Andre Agassi has been denied his 800th career victory and his Wimbledon preparations have been thrown into disarray. The multiple Grand Slam champion lost to Igor Andreev 4-6, 7-6, 7-6 at the Stella Artois Championships.
Agassi, who has been stuck on 799 career wins since March, has now lost three matches in a row - the first time this has happened since 1997.
Fellow-former Wimbledon champion Goran Ivanisevic also departed the $860,265 (468,000 pound) grasscourt warm-up tournament, beaten in the opening round by Romanian Victor Hanescu 6-7, 6-4, 6-4.
Mark Philippoussis followed the trend, his defeat the most surprising of all, against a Welshman ranked 849 places below him.
But defending champion Andy Roddick advanced smoothly, beating Slovak Karol Kucera 7-6, 6-2 in straightforward fashion.
"I wasn't hitting the ball super-clean, but I was able to get through it and came up with some clutch shots in the tiebreaker," he said.
Philippoussis, runner-up at Wimbledon last year and a former winner of the Stella Artois Championships, lost 7-6, 7-6 to Ian Flanagan in one of the biggest upsets in the tournament's history.
"It doesn't matter what someone is ranked when you get out there," Philippoussis said. "I just couldn't do anything."
Flanagan saw things differently. "A match like this makes you realise how good you can be," he beamed. "Hopefully I can go and have a good week."
Agassi's week is already ruined, by a Russian who has won only 14 senior matches since turning professional in 2002.
ANDREEV THRILLED
Winner of 58 singles titles, including all four grand slam titles at least once, Agassi had looked to be in good shape early on against a young Muscovite who had never played on grass until this week.
But Andreev, conqueror of Juan Carlos Ferrero at the French Open last month, turned things around as Agassi could find no answer to his big groundstrokes.
Agassi bolted from Queen's Club after the loss and is facing a fine for failing to fulfil his post-match obligations.
But Roddick, who is playing doubles with Agassi this week, said he was not concerned about his partner's slump.
"It happens with all players. He's not hitting the ball as well as he wants to in the matches. We've been practising and he's been practising great.
And we played doubles yesterday and he was hitting the ball perfect. If there's one thing I know, it's not to worry about Andre Agassi."
Andreev was thrilled as he left centre court, but the biggest smile of the day belonged to Flanagan.
Ranked 866 in the world, he had never played an ATP-level match in his life. "It will take a couple of days to sink in," he smiled after felling Philippoussis.
TURNED PRO
Victory in this one match will almost double his career's earnings Since turning professional in 2000, the Briton had made only $6,229. Tuesday's victory nets him at least $5,920.
"I was staying under Kew Bridge... now I'll be able to afford a hotel on it," Flanagan said.
"I've just got off the phone to (referee) Alan Mills and asked him for a wildcard into the Wimbledon main draw... we'll see what happens."
By contrast, Philippoussis is one of the biggest names in world tennis. He has reached the final of two Grand Slams, has been ranked as high as eighth in the world and has earned more than $6.5 million.
But on a scorching day at London's Queen's Club, the 22-year-old from north Wales matched Philippoussis point for point.
The Australian played poorly but still it was a major achievement for Flanagan and he kept his nerve to win in two tiebreak sets.
"That wasn't a great day, obviously," Philippoussis said. "I never felt comfortable out there.
"I'd never seen him play before... but I've got to stay positive. This is a bit of a setback but the big one's coming up, Wimbledon."