Earlier this year Roger Federer defeated Stefanos Tsitsipas in straight sets to capture the Dubai title and his 100th ATP tour-level championship. Twenty years ago, in October 1999, no one knew in the Brest, France, crowd knew they were witnessing a 20-time Grand Slam champion. 

"I don't believe there is a huge difference between the challenger tour and the ATP tour," Federer said. "But it really tests your spirits because they are always usually in the smaller cities of the country, and it's harder to get to. So you really build thick skin."

Federer rose from No. 66 to No. 57 after defeating Max Mirnyi in the Brest final, putting him on the verge of the Top 50 for the first time. This would be the first and only singles ATP Challenger win for the Swiss—earlier that year he won doubles with Sander Groen at an ATP Challenger in Segovia. Four years later, Federer would hold his first Grand Slam trophy at Wimbledon. 


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Federer has come a long way from that day in 1999, and at 38 years old he's showing no signs of stopping. This summer, he came close to claiming Slam No. 21 on the same grass courts, where he was just one point away before Novak Djokovic clawed his way back.

The other Big 3 members, Rafael Nadal and Djokovic, are still in their early 30s and are approaching his Grand Slam record. As yet another new season nears, who knows, maybe everyone will see a repeat of his 2018 and 2017 Australian Open victories. Anything is possible with Federer.