The Rotterdam tournament is heating up, with Wawrinka, who has declared he will retire after this season, giving his last performance. In the opening round, his match against Bugard almost created a record. The age difference was over 23 years, the second biggest gap in a tour match since 1990. What are the top matches in this category, and how did the protagonists develop later on?
1. 25 years and 11 months difference: Thiem (18) defeated Muster (44) at Vienna 2011
This was a passing of the torch between two Austrian legends. Muster was already 44 years old but still competed in his home tournament. His opponent was a rising star, 18-year-old Thiem.


Later on, Thiem, dubbed the “Prince of Clay,” did not follow Muster’s path but blossomed on hard courts, winning his only two major titles there.
2. 23 years and 3 months difference: Wawrinka (40) defeated Bugard (17) at Rotterdam 2026
Unnoticed, the late-blooming Wawrinka has reached the age of 40. The young star he defeated was still a minor. If he becomes famous in the future, will he remember this old-versus-young showdown?

3. 21 years and 8 months difference: Norman (38) defeated Betta (16) at ’s-Hertogenbosch 2009
Lower-tier tournaments often see such records. The German Norman once beat 16-year-old Betta on Dutch grass courts. However, Betta has since disappeared from the scene.

4. 21 years and 7 months difference: Alcaraz (17) defeated Feliciano López (39) at Marbella 2021
By comparison, these two are the most prominent among the five pairs in terms of fame and titles. Alcaraz needs no introduction; he is extraordinarily talented, achieving in his youth what many cannot in a lifetime. López, nicknamed “The Roman,” also appears on several age-related records, such as consecutive Grand Slam appearances.

5. 21 years and 5 months difference: Karlović (39) defeated Aliassime (18) at Pune 2019
Speaking of the retired Karlović, many fans consider him one of the best servers ever, while Aliassime was once one of the top prospects among the post-2000 generation. They delivered a memorable clash between two generations early that year on the Asian circuit.
How many memories do you still have of these matches from back then?(Source: Tennis Home, Author: Luo Cheng Qiye)