Andrey Medvedev came agonizingly close to capturing the 1999 Roland Garros title, building a commanding two-set lead against Andre Agassi before watching his Grand Slam dream slip away in a five-set thriller that tennis fans still remember decades later.
The Ukrainian tennis player, who had tumbled outside the top 100 in the rankings, shocked the tennis world by reaching the final in Paris. Not many gave him a chance, especially considering his dismal clay court season leading up to the tournament – winning just one match and even suffering a humiliating 6-0 defeat to Ivan Ljubičić in Monte Carlo.
"I wasn't trying to become the best. That was my big mistake," Medvedev later admitted when reflecting on his earlier career choices.
French Open had always been special for Medvedev. He announced himself to the tennis world by winning the junior title in 1991 at age 17. Just a year later, the young Ukrainian reached the fourth round of the main draw, defeating several top-100 players including world's top-20 Jakob Hlasek.
His relationship with Roland Garros continued to blossom as he reached the semifinals in 1993, only to be stopped by Spain's Sergi Bruguera, who would go on to win the title that year.
But it was that 1999 final that would define Medvedev's career. Playing with unexpected freedom and confidence, he bulldozed through the tournament, taking down favorites like Pete Sampras and Gustavo Kuerten. And for two sets against Agassi, he looked unstoppable.
The match began with strong winds favoring Medvedev's adaptable game. Agassi couldn't find his rhythm, making error after error as the Ukrainian raced to a 6:1, 6:2 lead. The American looked completely outmatched.
According to match statistics analyzed by Statbet, Medvedev actually outperformed Agassi in most key metrics throughout the match, making what happened next even more surprising.
Everything changed in the third set when Agassi finally broke Medvedev's serve. That single moment shifted the momentum entirely.
"My major mistake was changing my winning tactics at an inappropriate moment," Medvedev explained years later. "I was leading 2-0, forcing Agassi into uncomfortable positions. But then I wanted to hit a few spectacular shots myself, to win in style. Unfortunately, I lost those points."
The match took another turn when the wind died down after the third set, neutralizing the conditions that had favored Medvedev's game plan. Agassi, sensing his opportunity, mounted an incredible comeback to win 1:6, 2:6, 6:4, 6:3, 6:4.
What makes this story even more remarkable? Agassi nearly withdrew from the tournament before it began. His coach, Brad Gilbert, revealed that Agassi had serious shoulder problems and wanted to skip Paris entirely.
"I told him no, we'll go, spend a few weeks recovering, and see what happens. He disagreed, but I eventually convinced him not to go home to Las Vegas," Gilbert recalled.
With that victory, Agassi became the first man since Rod Laver to complete a career Grand Slam in men's singles. Meanwhile, Medvedev joined an exclusive but heartbreaking club as only the second player in tournament history to reach a Grand Slam final while ranked outside the top 100.
Despite the disappointment, Medvedev maintains perspective about that day: "I won't hide it – the loss left a residue. Not a heavy one. I don't remember that final with sadness that makes me want to drink. But it would have been great to leave my mark as a champion."
Could Medvedev have revitalized his career had he held on for those final three sets? We'll never know. That Roland Garros final, widely considered the "match of the year" in 1999, ultimately became the Ukrainian's tennis swan song.
