Federer first played Agassi at his home Basel Open tournament, 27 years ago, as he fell to defeat in straight sets, 3-6, 2-6.

Seven years later, they faced off one last time in the final of Agassi’s home tournament, the US Open, with Federer a heavy favorite, having won their previous seven meetings.

Federer extended his winning run to eight, as he beat the American in four sets, 6-3, 2-6, 7-6, 6-1, clinching his second straight title at Flushing Meadows.

Over the years, Federer and Agassi competed at legendary venues such as Arthur Ashe Stadium and Rod Laver Arena, but it’s fair to say that none matched the ‘heights’ of their exhibition contest in 2005.

Roger Federer played Andre Agassi on a helipad 600 feet above ground level in Dubai 20 years ago

Ahead of the 2005 Dubai Tennis Championships, Agassi and Federer took part in a once-in-a-lifetime exhibition contest on the Burj Al Arab’s helipad.

Playing 689 feet above the ground, the two tennis legends competed in one of the most iconic matches in the history of the sport.

The Dubai tournament director Salah Talak, claimed that the event cost just under $25,000 to put together, although it was certainly worth it according to the Swiss star.

“It was an unbelievable experience for me, doing it with Andre [Agassi], who is a legend of the game, and to promote the tournament here in Dubai, which is a tournament I love coming back to,” said Federer.

“Having this picture, this iconic picture of the two of us here in Dubai playing on the helipad where they created this court all alone, and the helicopter watching us do it.

“It was very special for us to do, it’s a special place in the world for sure.”

Agassi was also impressed, as he explained what was ‘weird’ about playing 600 feet above the ground.

“This is amazing, I’ll tell you, walking up here first of all when you get over the drama of being up so high, you come up those stairs and see they actually put a tennis court down here it’s quite a feeling,” he said.

“Once you start all you’re seeing is the ball again, it’s a free feeling out here, we were having a good time.

“Sort of weird when you toss it [the ball] though, feels like you’re tossing it a mile high.”

The pair coincidentally met in the 2005 Dubai Tennis Championship semi-finals, as fans anticipated a thrilling ‘rematch’, this time on ground level.

As was often the case when Federer and Agassi met, it was the former who came out on top, winning 6-3, 6-1, hitting an ‘impossible’ shot on his way to victory.

Roger Federer’s eight Dubai Tennis Championship titles

Eight of Federer’s 103 ATP Tour titles came in Dubai, as the 43-year-old dominated in the Middle East throughout his career.

Appearing in ten finals, the Swiss phenom secured wins over some of the world’s greatest players in the UAE.

Federer won his 100th ATP title in Dubai, six years ago, as he took down Stefanos Tsitsipas in the final, 6-4, 6-4.

No player has won more titles in Dubai than Federer, with Novak Djokovic, the only other multiple-time winner, currently sitting on five.

Djokovic won’t return to Dubai in 2025, as Federer’s record seems safe for now.

The 2025 Dubai Tennis Championships are set to begin on Monday, February 24.