Roger Federer, then 19, won his first ATP Tour title at 2001 Milan.

A Car Break In, A 'Terrible Mistake' And Federer's First Title

20 years ago today, Roger Federer captured his first ATP Tour Title in Milan

Twenty years ago — when Rafael Nadal was just 14, and 21-year-old Marat Safin sat atop the FedEx ATP Rankings — a baby-faced 19-year-old from Switzerland with a ponytail and a poetic one-handed backhand won his first ATP Tour title. Roger Federer’s celebration after beating Julien Boutter at the Milan Indoors 20 years ago this week was muted, almost as if he knew it was only the start of bigger things to come.

“I’ve had to wait a long time for this moment,” he said after earning $54,000 for the win. “It should get easier from here on out.”

102 titles, 20 majors and more than $100 million in prize money later, it’s safe to say that things did get a bit easier for the man who’s evolved into one of the world’s most celebrated and beloved athletes. But at the time, he had a more pedestrian concern to deal with: figuring out how to get back home after the match. According to René Stauffer’s excellent biography, Roger Federer: Quest for Perfection, Robert Federer, Roger’s dad, locked the keys in the car. He had to smash the window out so they could drive back to Switzerland.

Perhaps the smashing of the window foreshadowed the records his son would break, but in any case, many were surprised that it took Federer as long as it did to capture that first title. He was a top junior, having won Junior Wimbledon and the prestigious Orange Bowl tournament in Miami in 1998. After a 13-17 start on the ATP Tour in ’99, he won bronze at the Olympics in Sydney, where he and Mirka Vavrinec became a couple, and made it to the final of the Swiss Indoors Basel in his hometown.

He was clearly a future star, but no one was sure when that future would arrive.

“I didn't come in [to the match] thinking I was going to win the title, but I knew I was playing well indoors,” Federer said of that first title in 2001. He recalled near misses in 2000, losing in a third-set tie-break to Marc Rosset in the final of what’s now called the Open 13 Provence in Marseille and a tough five-setter to Thomas Enqvist in the final of the Swiss Indoors Basel.

“I played amazing against Enqvist and ended up losing … so I thought, ‘Oh, God here we go. I'm never going to win a tournament,’" Federer said. "And then when I won Milan, obviously I was extremely relieved and just very happy. I played great. It was a big moment for me.”

Boutter came into the match feeling poised to claim his first title as well. He beat Federer in their only prior match, in a Challenger event in Grenoble two years before. “He was already considered the future Pete Sampras, but at that time he was still untested and quite nervous on the court,” Boutter said in a January interview with ATPTour.com. “I was confident… it could have been my final.”

Federer beat Goran Ivanisevic and Yevgeny Kafelnikov to make it to the final against Boutter, who won fans a year later at the Australian Open when an opponent in a doubles match inadvertently hit and killed a bird that had been chasing a moth on court. Boutter rushed over to see if he could save it, but when he saw it was too late, he got down on his knees, crossed himself and gave the bird, a house martin, dignified last rites.

“I really wanted to win my first ATP title. That was a big week for me... I felt like I had pressure, because maybe I went into that final as a little bit of a favourite,” Federer recalled. “But it was fast indoors and Boutter was a big server, so you never knew what was going to happen.”

Boutter, a Frenchman then 26 and ranked No. 67, was in a far less compassionate mood against Federer in Milan that day. He went up a break on the Swiss teen in the first set and Roger, who used to be a lot more McEnroe-esque on court as a teen, threw his racquet in frustration. Boutter sensed an opening.

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Federer, looking sharp with his ponytail and a red and white kit befitting his Swiss heritage, stormed back to take the first set, 6-4, but fell behind again in the second set and lost it in a tie-break. Then the chair umpire made what Boutter still considers a “terrible mistake”. Federer should have served first in the third set but instead the chair umpire got mixed up and told Boutter it was his serve. If a familiar feeling of dread had taken root somewhere inside young Federer’s gut, he never showed it, breaking Boutter in that first service game and hanging on for a 6-4, 6-7(7), 6-4 win.

It took Federer nearly another year to win another title — in Sydney the following January — and later in 2002 he cracked the Top 10 for the first time. The next year, he was off to the races, going 78-17 with seven titles, including Wimbledon. The Milan Indoors became the Breil Milano in 2003, the Indesit ATP Milan Indoor the next year and the Internazionali di Lombardia in 2005, the tournament’s final season. While the event is gone, it’s clearly not forgotten. Milan now hosts the Next Gen ATP Finals.

The memory of losing to Federer remains vivid for Boutter, who retired in 2004 and is now the tournament director and co-owner of the Moselle Open, an ATP 250 event in Metz, France that’s scheduled to take place after the US Open. Ivan Ljubicic, Federer’s coach, told him two years ago that he and Roger had watched their Milan match on tape recently. Then Boutter bumped into Federer, who was still annoyed that he had lost to him back in Grenoble in 1999.

“He said that he never should have lost that match,” Boutter recalls.

Boutter says that he knew Federer would be a great player, but had no idea he’d win 102 more titles and become one of the all-time greats. He thinks the Milan story could have been different if he hadn’t lost serve in that third set when it should have been Federer’s service game after he had dropped the tie-break.

“I told Roger ‘Imagine if I had won that match, our careers would be switched’,” said Boutter, who reached a career high of No. 46 in the FedEx ATP Rankings in 2002. “He laughed and said ‘Yeah probably.’"

Federer admitted that he felt relief rather than joy and happiness — which kicked in 24 hours later — after triumphing in Milan. The Swiss remembers what he said to himself in the moment.

“At least I have one!”