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Best of 3: Biggest US Open upsets

September 11, 2015 - Roberta Vinci celebrates her win over Serena Williams in a women's singles semifinal match during the 2015 US Open at the USTA Billie Jean King National Tennis Center in Flushing, NY. (USTA/Pete Staples)

The US Open has seen its share of surprising results since the start of the Open era, in 1968. In this week’s Best of 3, we take a look at some of the three unbelievable upsets that shocked fans around the world.

Roberta Vinci d. (1) Serena Williams, 2-6, 6-4, 6-4 (2015 semifinals)

Vinci had carved out a successful doubles career that included a 2012 US Open women’s doubles title, but found herself tagged as a 300-1 underdog going into the match against Williams, who was just two matches from completing the first calendar Grand Slam since Steffi Graf in 1988. Ranked No. 43, the spunky Italian was competing in her first Grand Slam singles semifinal (compared to 47 for Williams) and had not taken a set from the world No. 1 in their four previous meetings.

It appeared to be business as usual when Williams cruised through the first set, but Vinci’s off-speed game of flat forehands, slice backhands and timely trips to the net began to frustrate her opponent. And in a moment that seemed inconceivable hours earlier, Vinci eventually reached triple match point on her serve and made good on her first chance with a forehand volley winner, covering her eyes in disbelief at recording a win which many have called the biggest upset in tennis history.

Vinci was asked during the post-match interview what made her believe she could win and, in a moment that summed up everyone’s reaction, she simply shook her head and said “No.” She would lose to Flavia Pennetta the following day in the first-ever all-Italian Grand Slam final but this May posted a career-high ranking of No. 7.

Alexander Volkov d. (1) Stefan Edberg, 6-3, 7-6, 6-2 (1990 first round)

Before winning back-to-back US Open titles in 1991 and 1992, the mellow Swede freely admitted he hadn’t yet learned to love the energy of New York. But he entered the 1990 US Open as the reigning Wimbledon champion and on a 21-match win streak – all of which prompted the world No. 52 Volkov to prepare for the match by booking a flight out for the following day.

The Russian left-hander served brilliantly and rifled passing shot winners on many of Edberg’s net approaches. He broke Edberg twice in the final set and clinched the shocking victory when the world No. 1 netted a forehand on match point.

The attention afterward proved to be too much, however, and Volkov bowed out in the next round to American Todd Witsken. Still, he would go to reach the US Open quarterfinals in 1992 and the semifinals in 1993, achieving a career-high ranking of No. 14 that year.

(Q) Julie Coin d. (1) Ana Ivanovic, 6-3, 4-6, 6-3 (2008 second round)

Ranked No. 188, Coin had never competed in the main draw of a Grand Slam or WTA tournament prior to arriving in New York, and she had pondered quitting the sport just weeks earlier. After coming through qualifying and winning her opening round, the fast-serving Frenchwoman showed no signs of nerves while competing against the world No. 1 and reigning French Open champion.

Ivanovic was far from her best, hitting 34 unforced errors and eight double faults, but Coin’s go-for-broke style didn’t allow the Serb to get into a rhythm. She converted on her third match point after Ivanovic sent a forehand long and let out a shriek of delight, marking the first time in the Open era that the top women’s seed had lost before the third round at the US Open.

The win left Coin as arguably the greatest one-hit wonder in tennis history. She would go on to compete in eight more Grand Slam main draws in her career and finished in the Top 100 in 2008 and 2009, but she never again advanced past the second round in a major and announced her retirement last December.