Seeds Fernando Verdasco, Sloane Stephens and Sam Stosur all suffered first-round exits as Wimbledon got underway on Monday.
Verdasco lost a dramatic five-set quarter-final against eventual champion Andy Murray at last year's tournament but was sent tumbling much earlier this time around, with Marinko Matosevic beating him 6-4 4-6 6-4 6-2.
Matosevic, who reached the last eight at Queen's, battled past 18th-seed Verdasco in two hours and 16 minutes.
On the women's side, Stephens' streak of reaching the second week at six consecutive grand slam tournaments ended with a 6-2 7-6(6) first-round loss to world No.109 Maria Kirilenko of Russia.
Stephens saved five match points serving at 5-6, sending it to a tie-breaker where Kirilenko clinched the match after a wide forehand by Stephens.
An American seeded 18th, Stephens had held the longest active run of fourth-round appearances at grand slam by a woman, dating to a semi-final showing at the Australian Open.
At Wimbledon last year, Stephens got to the quarter-finals, where she lost to eventual champion Marion Bartoli.
Also losing in the first round was former US Open champion Sam Stosur, who fell 6-3 6-4 to former US Open semi-finalist Yanina Wickmayer.
The defeat continued the Australian's poor run at Wimbledon, where she has never advanced past the third round and where she has lost in the first round six times in her 12 appearances at the All England club.
Stosur recently split with her coach, Miles Maclagan, just seven months into their partnership. The 2011 US Open champion hasn't reached the semi-finals in any tournament since Hobart in January and in recent weeks lost on grass in the second round at Birmingham and the first round at Eastbourne.
In other results on Monday, French Open semi-finalist Ernests Gulbis progressed safely to the second round after seeing off Juergen Zopp 7-6(7) 7-5 7-6(10) in three tight sets.
Victoria Azarenka also won her first match since returning last week from three months out, beating 1999 semi-finalist Mirjana Lucic-Baroni 6-3 7-5.
Two-time semi-finalist Azarenka, the eighth seed this year, has missed a large chunk of the season with a foot injury.
Japanese veteran Kimiko Date-Krumm, 43, lost 3-6 6-4 7-5 to Ekaterina Makarova of Russia.
Date-Krumm, who reached the semi-finals at Wimbledon 18 years ago, was the oldest player entered in the tournament this year. She made her Wimbledon debut in 1989, a year after Makarova was born.
Date-Krumm made 47 unforced errors in the two hour and 24-minute match.
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