Where the three oldest active players in the ATP top 100 were ranked 20 years ago

A new era has arrived in tennis, headlined by the world’s two best players, Carlos Alcaraz and Jannik Sinner.

Alcaraz and Sinner, aged 22 and 24 respectively, have dominated on the ATP Tour for the last two years, splitting the last nine major crowns between them.

Along with the Spaniard and the Italian, young stars such as Joao Fonseca and Learner Tien are climbing up the rankings, in what is shaping up to be another golden era in tennis.

However, there are still a number of veterans from the previous era still performing at the highest level.

The rankings of Novak Djokovic, Stan Wawrinka and Marin Cilic in 2006

The oldest player inside the current ATP top 100 is world number 98 Stan Wawrinka, who is set to retire at the end of the 2026 season.

Novak Djokovic is the second oldest at 38, ranked third, followed by 37-year-old Marin Cilic, who is placed 43rd.

All three former Grand Slam champions have been on the tour for over two decades, and 20 years ago, both Djokovic and Wawrinka were still inside the top 100.

The Serb, 18 years old in February 2006, was 72nd in the rankings at that time, while the Swiss star was 18 places above him in 54th.

Cilic was 17 years old and had already cracked the top 500, with the Croatian ranked 485th in the world.

The last time Novak Djokovic played Stan Wawrinka and Marin Cilic

Djokovic’s head-to-head record against Cilic is one of the most lopsided in history, with the 24-time Grand Slam champion leading 20-2.

The last time they played was at the 2025 Shanghai Masters, where Djokovic came out on top once again in straight sets.

Wawrinka has enjoyed slightly more joy against Djokovic over the years, having picked up six wins in their rivalry.

His last meeting with Djokovic also ended in defeat, however, with Wawrinka losing to him for the 21st time at the 2023 Wimbledon championships.