Welcome to Wimbledon Rewind, where wtatennis.com will take a look back at some of the most memorable matches from the past two decades at the All England Club. From notorious upsets to great escapes, rewind the clock and check out our list of the Top 8 second-round matches, laid out in chronological order.

Wimbledon Round Reviews
Gauff ascends, Serena survives through first round thriller

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2004: Gisela Dulko def. [W] Martina Navratilova, 3-6, 6-3, 6-3 
In 2004, Maria Sharapova famously made a breakthrough run to her first Grand Slam title and was crowned the next big tennis star. But elsewhere in the draw, another big star was making her last stand.  

Read more: Navratilova shows her class at 46 to win title 20 alongside Paes

47-year-old Martina Navratilova had already retired from tennis in 1994 after a legendary career, which earned her an induction into the International Tennis Hall of Fame in 2000. But Navratilova still had more in her, and returned to the doubles circuit later that year. After claiming the 2003 mixed doubles title at Wimbledon, she was awarded a surprise wildcard into singles, where she became the oldest player to win a Grand Slam singles match in Open Era. 

Navratilova bowed out gracefully in the second round after a three-set battle against a young Gisela Dulko. The 19-year-old from Argentina was making her main draw debut, but showed her grit to turn around a set deficit and win, 3-6,6-3, 6-3. 

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2006: [W] Agnieszka Radwanska def. Tsvetana Pironkova 7-5, 7-6(5)
The outer courts of Grand Slam tournaments have witnessed many future tennis stars grinding away in hopes of making it to Centre Court. In 2006, it was Polish youngster Agnieszka Radwanska, last year’s junior Wimbledon champion, making her senior debut with a wildcard.  

After overcoming another future star - you might have heard of Victoria Azarenka - in the first round, Radwanska was pitted against the rising Tsvetana Pironkova, who had turned heads at the 2006 Australian Open after taking down Venus Williams in her opening round. 

It was an intriguing clash between the two cerebral players, with Radwanska eventually edging past the Bulgarian in a tight straight sets victory, 7-5, 7-6(5). Radwanska ultimately lost to No.2 seed Kim Clijsters in fourth round - but six years later she would become Poland’s first Grand Slam singles finalist at Wimbledon. 

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2008: [1] Ana Ivanovic def. Nathalie Dechy, 6-7(2), 7-6(3), 10-8
Weeks after claiming the title at Roland Garros, the new World No.1 Ana Ivanovic came within an inch of crashing out in the second round at her next Grand Slam venture.  

Ivanovic had cruised in the first round against Rossana de los Rios, dropping just three games. When she took the court against France’s Nathalie Dechy, another unseeded player, she was likely expecting much of the same, especially after taking a 3-0 lead in the first set. But Dechy was once a Top 15 player, and things were about to get interesting for Ivanovic. 

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Ivanovic dropped the first set in a tiebreaker as Dechy came roaring back, and was under pressure throughout the second. The most nerve-wracking moment came at 5-4, where a miss-hit Ivanovic forehand gave Dechy two match points - Ivanovic saved the first, and then a heart-stopping net cord ball went the Serbian’s way to save the second. After that, the World No.1 was back in it, prevailing in an epic 6-7(2), 7-6(3), 10-8 victory - making sure to thank the net tape with a kiss.  

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2011: [W] Sabine Lisicki def. [3] Li Na, 3-6, 6-4, 8-6
21-year-old Sabine Lisicki was contemplating retirement in 2010, after she suffered an ankle injury so serious that she had to relearn how to walk and spent five months away from the courts. Known for her booming serve, which holds the record for being the fastest in women’s tennis, Lisicki was one of the game’s rising stars, but her ranking fell to as low as No.218 as she struggled to make her comeback. 

But back on her beloved grass courts, Lisicki finally returned to the winner's circle after lifting the trophy in Birmingham. Coming into Wimbledon, the wildcard was now a dark horse ready to wreak havoc on the draw - and newly-crowned Roland Garros champion Li Na would be her next casualty. The No.3 seed took the first set, but was unable to convert on two match points in a third set that went down to the wire as the German walked away with the upset, 3-6, 6-4, 8-6. 

 Lisicki went all the way to the semifinals, where she lost to Maria Sharapova. It was her best Grand Slam result, until she eventually went one round further at 2013 Wimbledon. 

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2011: [23] Venus Williams def. Kimiko Date, 6-7(6), 6-4, 8-6
Elsewhere in the draw, Centre Court was stunned silent when 40-year-old Kimiko Date, the second-oldest woman to ever reach the second round at Wimbledon, broke Venus Williams in her first two service games. Venus was a five-time champion at the All England Club, while her Japanese opponent Date had retired from tennis in 1996 but found her way back to the courts 12 years later.

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Date built up a daunting 5-1 lead, but Venus never gave up on the set. She pushed the Japanese player with her powerful groundstrokes, but couldn’t find her rhythm as Date eventually won the tiebreak. Date couldn’t keep up her momentum in the second set, and Venus was back in it to send them into a decider. Venus eventually prevailed after a nearly-three hour battle to win 6-7(6), 6-4, 8-6, and the pair walked off the court to a standing ovation after their titanic performance.  

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2016: [3] Agnieszka Radwanska def. Ana Konjuh, 6-2, 4-6, 9-7
Former Wimbledon finalist Radwanska was playing the best tennis of her career after winning the WTA Finals and returning to World No.2. She was one of the players in contention for the WTA No.1 ranking, but was almost stopped in the second round by 18-year-old Ana Konjuh in a highly entertaining three-set battle.  

Konjuh seemed in control of her destiny as she recovered from losing a one-sided first set 6-2 and found her game to win the second 6-4. She had Radwanska on the ropes, and held three match points as she served for the set twice - but destiny had other ideas. Konjuh suffered an unfortunate ankle injury as she was serving out the match, rolling her ankle and requiring extensive treatment. Although she bravely returned to the court to finish the match, she wasn’t able to win another point as Radwanska escaped with the victory.  

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2017: [6] Johanna Konta def. Donna Vekic, 7-6(4), 4-6, 10-8
Going into Wimbledon 2017, it seemed the weight of a nation’s expectations was on Johanna Konta’s shoulders. After a breakthrough 2016 saw her reach her first Grand Slam semifinal, make her Top 10 debut and win her first WTA title.  

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 Konta began the 2017 grass court season as the No.1 seed in Nottingham, going all the way to the final before being upset by Donna Vekic. She would soon get her chance at revenge, taking on the Croat in the second round at Wimbledon. The match unfolded from a baseline battle between the two big hitters and evolved into a service masterclass - at one point, both players held serve for 22 consecutive games.

Eventually it was Konta who emerged victorious, thrilling Centre Court with the 7-6(4), 4-6, 10-8 victory after a marathon three hours and 10 minutes. Konta eventually reached the semifinals, recording the best Wimbledon finish of her career. 

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2019: Dayana Yastremska def. [27] Sofia Kenin, 7-5, 4-6, 6-3 
Tennis fans got an early look at what could prove to be an emerging rivalry during last year’s Wimbledon, as unseeded Dayana Yastremska stunned No.27 seed Sofia Kenin in a thrilling three set clash.  

Read more: Yastremska takes control to upset Kenin in youthful Wimbledon thriller 

19-year-old Yastremska was making her highly anticipated pro debut after turning heads during her junior years by reaching the 2016 Wimbledon girls final, and had already racked up three WTA International-level titles. She was up against 20-year-old Kenin, who was having the best season of her career after lifting two trophies and breaking the Top 30 for the first time.  

The clash between two of the game’s brightest rising stars was also a great clash of styles, with Yastremska, one of the most aggressive players on tour, trying to blast through Kenin’s solid counterpunching. Yastremska eventually emerged victorious, sealing the upset 7-5, 4-6, 6-3.

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