Richard Krajicek stunned the tennis world when he won Wimbledon in 1996, pulling off one of the biggest surprises of the decade. Nearly 30 years after his career-defining victory, Krajicek—now a major tournament organizer—has not shied away from bold statements about the sport, including his opinion on the heated debate between Roger Federer and Novak Djokovic.

During his playing days, Krajicek competed in an era dominated by Pete Sampras, the king of grass courts. Between 1993 and 2000, Sampras won every Wimbledon title except for one—1996. That year, Krajicek delivered the upset that rocked the tennis community.

Krajicek had struggled in the previous two Wimbledon tournaments, exiting in the first round both times. Reflecting on those years, he admitted: “I wasn’t motivated to play. During my career, I fought myself as much as I fought my opponents.”

He described his struggles with perfectionism: “There were times in practice when my coach would shake his head. My attitude wasn’t bad—not even that. I was just driving myself crazy. I was too much of a perfectionist.”

Richard Krajicek of Holland holds the trophy aloft after his victory in the Men’s Singles event at Wimbledon in London. (IMAGO / Action Plus)

His first—and only—Wimbledon trophy

In a bid to change his fortunes, Krajicek borrowed a strategy from Andre Agassi, who had trained on hard courts before winning Wimbledon in 1992. Krajicek did the same leading into the 1996 tournament. “I hit on hard courts for about 20 minutes a day, and I started to feel really good with the ball,” he said.

His run at Wimbledon began with a dominant win over Spain’s Javier Sánchez Vicario, followed by victories over Australia’s Brett Steven and Germany’s Michael Stich. Then came his monumental quarterfinal clash with Sampras. Against all odds, Krajicek defeated the American star in straight sets, shocking the tennis world.

At 25, Krajicek’s Wimbledon triumph seemed like the beginning of a long reign, but his career didn’t take the trajectory many expected. While he went on to win 14 more titles, he never replicated his Grand Slam success. Plagued by injuries, he retired in 2003 at the age of 32 due to a chronic right elbow issue.

If my arm starts hurting after just a few serves, you have to be realistic. That’s why I’ve decided to stop,” Krajicek said upon announcing his retirement. “I achieved more and went higher in the world rankings than I ever dreamed as a kid.”

Federer vs. Djokovic debate

Today, Krajicek remains deeply involved in the sport as a key figure behind the ATP 500 tournament in Rotterdam. He’s also made headlines for his candid takes on tennis’s greatest players—particularly when he stirred controversy by siding with Novak Djokovic over Roger Federer.

I think Djokovic is more complete than Federer. Novak was able to win all four Grand Slam titles between 2015 and 2016. Roger was never able to do that,” Krajicek stated in 2018.

He elaborated on Federer’s dominance in his early years, noting the lack of serious competition during that time: Nadal couldn’t challenge him on other surfaces besides clay. It was a transition period. Roger played against stars from the previous generation like Agassi and Safin for a couple of years. The players of his age—Roddick, Hewitt, Ferrero, Davydenko, or Ljubicic—didn’t have the weapons to hurt him in Grand Slams.