A quarter of a century has passed since a 19-year-old Roger Federer lifted his first ATP Tour trophy, a moment that marked the beginning of his historic career. Long before the records, the rivalries and the reverence, there was Milan, the city where Federer first learned what it felt like to finish the job.
By the time the then-19-year-old arrived in northern Italy in February 2001, Federer was no longer just a promising teenager trying to break through. He had already reached two ATP Tour finals the previous season, in Marseille and Basel, only to fall short on both occasions. Those defeats stung, but they also served as an education. Ranked inside the Top 30, Federer felt closer than ever and it was no longer a question of if he would win a title, but when.
The draw in Milan was anything but forgiving. Federer’s path to the final included victories against Goran Ivanisevic and Yevgeny Kafelnikov, names synonymous with major glory and big-match experience. For a young player still learning to manage expectations and nerves, it was a demanding test of belief.
Federer moved past Rainer Schuettler and Cyril Saulnier in his first two matches and then took out Ivanisevic in straight sets in the quarters. The Croatian Ivanisevic would go on to win Wimbledon just a few months later.
Standing between Federer and a third tour-level final was Kafelnikov, who arrived in Milan at No. 7 in the PIF ATP Rankings. On paper, the former World No. 1 Kafelnikov appeared the favourite among the remaining semi-finalists, a group that also included Julien Boutter and Greg Rusedski.
“Out of the four guys in the semis, I felt the title was in my hands,” Kafelnikov told ATPTour.com.
Kafelnikov had beaten Federer in all three of their previous Lexus ATP Head2Head meetings, yet he recalls that even then, the sense of anticipation surrounding the young Swiss was impossible to ignore.
“We all knew that Roger was the best junior at the time,” Kafelnikov said. “I remember playing him for the first time in Rotterdam when he was still 18. It took me three sets to get past him. I knew all he needed at that time was someone who could lock him up in the frame of mind when he could be really focused on his tennis.
“[He was] playing the PlayStation with the coach. He was not so focused compared to when he turned 22, when he started to really believe that he could be No. 1. He had the game to be the best player in the world, we all knew that.”
Federer backed that belief on court, battling past Kafelnikov 6-2, 6-7(4), 6-3 to earn his first victory against the ATP No. 1 Club member and secure his place in the Milan final. Awaiting him in the championship match was Frenchman Boutter, contesting his first tour-level final.
Federer claimed the opening set 6-4, but Boutter pushed him to the edge in a tense second-set tie-break, which the Frenchman won 9/7. For a teenager still chasing his first title, it was a familiar danger moment. Instead of faltering, Federer reset. He steadied his nerves, trusted his instincts and closed out a 6-4, 6-7(7), 6-4 victory to finally lift his first ATP Tour trophy.
“I really wanted to win my first ATP Tour title,” Federer once told the ATP. “That was a big week, beating Boutter in the final. It felt like I had pressure because maybe I went into that final a little bit as the favourite. But it was fast indoors and Boutter was a big server, so you never knew what was going on.
“I think it was more of a relief rather than joy or happiness. I think that kicked in 24 hours later. I remember I thought, 'At least I have one'.”
The triumph was a milestone years in the making. Federer had earned his first ATP Tour match win in Toulouse in 1998, three years before Milan, and then steadily climbed the rankings.
“I am a really small space in the career of Federer,” Boutter said. “I am the first one to lose in a final against him, but many guys did the same as me."
With the benefit of hindsight, Milan stands as a defining early chapter rather than an isolated success. Federer would go on to capture 103 tour-level titles, including 20 Grand Slam crowns, with his final triumph arriving in Basel in 2019.