Lori McNeil v Steffi Graf (1994)
Steffi Graf, one of the most dominant performers in tennis history, captured her first Wimbledon singles crown in 1988. That was the year she notched an incredible Golden Slam by emerging victorious at all four majors as well as in the Seoul Olympics.
Six years later, Graf was still ruling the roost. She began in 1994 by triumphing at the Australian Open in Melbourne and before reeling off a succession of title triumphs in Tokyo, Indian Wells, Delray Beach and Miami.
Understandably big things were expected of her at Wimbledon, where her first-round clash was against Lori McNeil, an unheralded American.
Graf had suffered a previous defeat to McNeil in a routine WTA Tour event in Houston in 1992. But few anticipated problems for the record-breaking German on the grass at Wimbledon, where she had farmed the trophy in five of the previous six years.
After an early weather break at 5-5 in the first set, McNeil took the opener 7-5 when Graf double-faulted on set point – and the American went on to show admirable nerve when sealing the upset via a second-set tiebreak.
The oddsmakers slashed McNeil’s odds to go all the way from 100/1 to single figures, but her brave run ended in the semi-finals against Spain’s Conchita Martinez, who would go on to lift the title.
McNeil’s opening-round triumph over Graf was the first time a women’s singles defending champion had lost in the round of 128. However, that was far from the end for Steffi, who roared back to nail the grass-court championship crowns in 1995 and 1996.
Jelena Dokic v Martina Hingis (1999)
Martina Hingis was the ‘it’ player in the late 1990s, but while the Swiss miss was a huge talent she wasn’t unbeatable.
At Wimbledon in 1999 Hingis, then world number one, was humbled 6-2 6-0 by promising 16-year-old Australian Jelena Dokic.
Hingis had been just 1/33 to waltz in the last 64, but with the defeat she became only the third top-ranked player to lose in the opening round of a women’s Grand Slam in the Open era.
Dokic, who had already come through qualifying, had occasionally practised with Hingis and there was most definitely no fluke about the outcome.
The world No. 129, whose was coached by her fiery father Damir, went on to defeat Grand Slam heroine Mary Pierce before falling in the quarter-finals against another qualifier in the shape of America’s Alexandra Stevenson.
Pete Sampras v George Bastl (2002)
Few players have dominated the grass game like Pete Sampras, but when the time came for the American to relinquish his grip on Wimbledon, it was as if he fell of a cliff.
The seven-time champion had lost to Roger Federer in the last 16 in 2001, but Sampras still looked a major force in the fast-court Grand Slams.
After easing through his All England Club opener in 2002, Sampras met Switzerland journeyman George Bastl, who was ranked 145th in the world, in round two.
Bastl had earlier lost in qualifying but gained entry to the main draw as a lucky loser when another player was injured. The Swiss stand-in had failed to win a match on the main tour that year and had competed principally in lower-level Challenger Tour events.
However, Sampras looked a pale imitation of the player he had once been and Bastl pulled off an amazing 6-3 6-2 4-6 3-6 6-4 triumph.
But any thoughts that the game was up for Sampras were unfounded as he staged a stirring recovery to win his 14th and final Slam singles at the US Open later that year.
Mario Ancic v Roger Federer (2002)
After the Wimbledon victory of big-serving Goran Ivanisevic in 2001, there were high hopes that Roger Federer would replace Pete Sampras as the next multiple grass-court champion and few bookmakers envisaged any problems for the young Swiss ace in his opener against Croatia’s Mario Ancic in 2002.
But Federer, seeded seventh that year after ending Sampras’s 31-match winning streak at Wimbledon on the way to the 2001 quarter-finals, was felled 6-3 7-6 6-3 by little-known 18-year-old qualifier Ancic, who was born in Ivanisevic’s home town of Split.
Ancic, the second youngest player in the 2002 main draw, broke Federer’s serve twice in the opening set and the 2000 Wimbledon juniors finalist went on the take set two, via a tiebreak, and set three to win in just an hour and 40 minutes.
Eleni Daniilidou v Justine Henin (2005)
In 2005 Belgium’s Justine Henin went to London on a winning streak of 24 matches and so it was no surprise that her first-round opponent Eleni Daniilidou was available at double-figure odds to progress to round two.
Henin had come up short against the Greek in the Den Bosch semi-finals in 2002 so was aware of the potential danger.
The pair produced an epic three-set contest in which both players were treated for injury issues – Henin a hamstring problem and Daniilidou a leg injury.
The favourite, whose favourite surface was clay, managed to save two match points in the final set but her serve ultimately let her down as her 11th double fault of the match afforded the unheralded Daniilidou a 7-6 2-6 7-5 victory.