Stan Wawrinka carved out a piece of tennis history by defeating Thijs Boogaard at the Rotterdam Open.
The Swiss star defeated the Dutch teenager in straight sets to set up a quarter-final match with Alex de Minaur.
Wawrinka has impressed on his retirement tour and his Rotterdam Open match was the second largest age gap in history.
There was 23 years and 100 days between Wawrinka and Boogaard, which can only be beaten by one match in tennis history.
The biggest age gap match in tennis history
There is only one match that can beat Wawrinka’s latest triumph, and it will take some beating in tennis history.
At the Vienna Open in 2011, 44-year-old Thomas Muster faced an 18-year-old Dominic Thiem on home soil.
Muster had been retired for 11 years, but came out of retirement briefly, before facing Thiem in his last-ever match.
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Thiem overcame the Roland Garros champion in straight sets at the indoor event, winning the tie by 6-2, 6-3.
Muster retired on the spot after losing to his teenage compatriot, in one of the biggest passing of the torch moments in the sport.
“This is such a great goodbye. This is definitely my last appearance on the ATP,” he added in his on-court interview.
“It was my last match, it was very exciting to end it in Vienna and very emotional. It was such a send-off. I didn’t know whether to cry or play.”
Thomas Muster and Dominic Thiem’s brief coaching partnership
Bizarrely, Muster and Thiem had already worked together nearly two years before their history-making match.
Thiem hired Muster as his coach ahead of the Australian Open, with the hope that the Grand Slam winner could help him win his own major.
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However, they ended their partnership just two weeks later because their working styles and characters did not match.
Thiem said the partnership ‘did not fit’, but the Austrian clearly made the right decision as he lifted the US Open title just seven months later.
The Austrian was working with Günter Bresnik and Nicolás Massú during his biggest achievement in tennis.
