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12/3/08 10:30 PM | Jonathan Morgan
After winning the Orange Bowl in late 1998, Federer was done with the juniors and ready to make a jump into the main tour.
Roger Federer began 1999 ranked just outside the top 300. He tried and failed to qualify for the Australian Open in January, and returned to Europe to try his hand indoors.
He qualified for a Challenger event in Germany in late January and reached the semis. The following week, he was granted a wild card into the Marseille event and did not disappoint. 17-year-old Federer, ranked 243rd, took out Carlos Moya in the first round. The same Moya who just the previous year had won the French Open and was ranked 5th in the world when Federer beat him. It was Federer's biggest win of his career. Although he lost in the quarterfinals to Arnaud Clement, he was improving very quickly.
Rotterdam offered Roger a wild card into the qualies there, where he qualified and again reached the quarterfinals. After this result his ranking jumped up to 129th. However, Federer was notorious in his youth for being a complete headcase and unable to string together some good results or keep up his level of play for extended periods of time.
After Rotterdam, the Swiss went 2-5 in his next few events, although one of his wins was a fine four-set victory over Davide Sanguinetti in his first Davis Cup appearance. Federer was bagelled by Vince Spadea in Monte Carlo that year, one of only four he has received in his entire career.
It was May before Federer got back to his winning ways. He qualified for a Challenger in Slovenia and made the semis, boosting his ranking up to a career high of 115th. He then competed in Roland Garros as a wild card and faced Patrick Rafter, the No. 3 player in the world at the time. Federer took a tough opening set but lost in four, including the second bagel of his career.
Federer got back on his beloved grass and made the semis of the Challenger event in Surbiton before losing to Sargis Sargsian in a very tight three-setter. The rest of his grass season and then some, however, was wretched. Byron Black crushed him in Queens, dishing him his third bagel of his career. He failed to qualify in Nottingham and lost in five sets at Wimbledon's first round. Losses in Gstaad, a pair of tight losses in Davis Cup against Belgium, second round at the Segovia Challenger, Washington, and failing to qualify for both Long Island and the US Open seemed to bring Federer back down to Earth.
He scored a win in both Tashkent and Toulouse following the US Open, but Federer just couldn't get any consistency. At that point, he had turned 18 and received a wild card into Basel. It was there where he got his mojo back. A quarterfinal loss to Tim Henman followed by a semifinal run in Vienna the following week got Federer back on track and his ranking shot up to 67th.
In Lyon, as a special exempt, he won the first round but lost another tight three-setter to Hewitt. With his confidence on high, Federer went back down to the Challenger tour and won the title in Brest, France. A failed qualifying attempt in Stockholm ended his year. His results were up and down and his ranking was 65th at the close of the year. It was a great first year on the tour for Federer, all things considered.
2000 opened with losses before the Aussie Open but his best slam result of his career with a third-round showing in Melbourne. Federer's game looked solid as he beat Mark Philippoussis in a tough four-setter in Davis Cup before once again falling to Hewitt in the reverse rubber. The Swiss was up 2-1 but lost the final two rubbers to lose the tie.
Federer's indoor season was once again fantastic. In Marseille he had a great run to the finals but lost in a third-set tiebreaker to Marc Rosset. Quarterfinals in London and semis in Copenhagen cemented this time of the year as Federer's best thus far in his career. After Copenhagen, Federer's ranking was up to 49th.
Like the previous year, Federer didn't make much of an impact in either the US or the clay season, going 1-7 until the French Open. He came out of nowhere to make the fourth round there, beating out fellow Swiss Michel Kratochvil 8-6 in the fifth for his first five-set win. He lost to Alex Corretja in the fourth round, and followed up this fine tournament with a quarterfinal run in Halle on the grass, bumping his ranking up to 35th.
With the young Federer, for every up, there was a down. After Halle, he went 1-6 until the US Open. The one win was over Vladimir Votchkov in five crazy sets to get Switzerland back into the World Group. One of the losses was to Hewitt in Canada in three sets. Federer then made the third round at the US Open before losing to fellow young gun Juan Carlos Ferrero in four tight and exhilarating sets.
Roger's next three events bumped the recently turned 19-year-old into the top 30. It was at the Olympic games in Sydney where he not only met his longtime girlfriend Mirka, but also made the semifinals, losing to Tommy Haas. A tough loss to Arnaud Di Pasquale meant Federer would go home without a medal. The hunger for wins seemed to get to Federer, as he returned to the Euro indoors with a semifinal run in Vienna and a finals appearance in his home Basel event. In the semis in Basel, Federer scored his first win over Hewitt, a tough three-set victory that ended 8-6 in a third-set 'breaker. He then went on to lose in the final to Thomas Enqvist in five sets. Reports allege that the young Swiss maestro cried profusely after the final.
Mediocre appearances for the rest of the season saw Federer finish the year ranked 29th. His first win over Hewitt, a few tour finals, and a bunch of five-setters marked his performances prior to turning 20. Federer would enter 2001 as one of the players many people pegged as a future star.
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