Stan Wawrinka joins Roger Federer and Jimmy Connors as only 38-year-olds to reach Wimbledon 3R in 45 years

Stan Wawrinka joined an illustrious club with his second-round win over 29th seed Tomas Martin Etcheverry on Thursday. The 38-year-old Swiss has impressed in his first two matches at SW19 this week. After beating young Finn Emil Ruusuvuori in the first round, he took out the higher-ranked Etcheverry in four sets.

The pair split the first two sets before Wawrinka dropped only six games in the last two sets to reach the third round at Wimbledon for the sixth time. It's the first time the three-time Grand Slam champion has ventured beyond the second round since reaching back-to-back quarterfinals in 2014–15.

In the process, Wawrinka joined Roger Federer (2021) and Jimmy Connors (1991) as the only 38-year-old players in the last 45 years to reach the third round at the grasscourt Major.

Unlike eight-time champion Federer and two-time winner Connors, Wawrinka has never been beyond the last eight at Wimbledon.

The 38-year-old is now 22-16 at the grasscourt Major but faces a tall task against four-time defending champion Novak Djokovic on Friday. Stan Wawrinka has won only six of his 26 meetings against the Serb.

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How Stan Wawrinka has fared against Novak Djokovic in Grand Slams?

Stan Wawrinka is in the Wimbledon third round.

Stan Wawrinka has a rather lopsided record against Novak Djokovic, but the Swiss has fared rather well against Djokovic in Grand Slams. The pair has met eight times in Majors, with each player winning four times. Their first Major clash was in the 2012 US Open fourth round, which Djokovic won in four sets.

A few months later, they met again in the 2013 Australian Open fourth round, where the Serb escaped with a 12-10 win in the fifth. Another five-setter ensued in their US Open semifinal that year, which again went Djokovic's way.

However, Wawrinka would soon have his revenge, beating the then-three-time defending champion in the 2014 Australian Open quarterfinal en route to taking the title.

Although Djokovic avenged that defeat by beating the Swiss in the semifinals in Melbourne the following year, Wawrinka would avenge the defeat in the Roland Garros final a few months later.

The defeat meant Djokovic was denied the opportunity to emulate Rod Laver as the only male player in the Open Era to win the calendar Grand Slam.

Wawrinka wouldn't stop there, beating Djokovic in the 2016 US Open final and the 2019 US Open fourth round. If he wins again this week, Wawrinka will join Federer as the only players to beat Djokovic at all four Majors.