5 players who have lost more ATP 500 finals than Stefanos Tsitsipas ft. John McEnroe

Stefanos Tsitsipas failed to get past Novak Djokovic in the final of the Astana Open on Sunday. Following the loss against the Serb in Kazakhstan, Tsitsipas has now lost every single ATP 500 final that he has played in over the course of his career.

The Greek first made the final of an ATP 500 event at the 2018 Barcelona Open, where he went down to Rafael Nadal. Roger Federer got the better of Tsitsipas in the final of the Dubai Championships a year later, while Dominic Thiem did much the same at the 2019 China Open.

Tsitsipas made it to the final in Dubai yet again in 2020 but was defeated by Djokovic before Andrey Rublev won the title round at the Hamburg European Open the same year.

Alexander Zverev beat the Athenian in Mexico last year while Nadal won the Barcelona final against Tsitsipas yet again in 2021. Felix Auger-Aliassime won the Rotterdam Open earlier this year at the expense of the Greek.

Here's a look at five players who have lost more ATP 500 finals than Stefanos Tsitsipas in the Open Era:

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#5 Arthur Ashe - 10

Arthur Ashe won 48 of his 76 singles titles in the Open Era but also lost 10 finals in the ATP 500 category.

Between 1970 and 1976, Ashe ended up as the runner-up 10 times at ATP 500 tournaments, beginning with a loss to Cliff Richey in Washington. He also lost to Tom Okker in the 1975 Paris Indoors and Ilie Nastase in the final of the WCT Challenge Cup in 1976.

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#4 Ken Rosewall - 10

Ken Rosewall also ended up as the losing finalist in 10 ATP 500 finals between 1968 and 1977. Notable among the title round clashes were those against his legendary compatriots Rod Laver and John Newcombe.

Laver defeated Rosewall to win at Wembley in 1968 while Newcombe defeated Rosewall in the 1972 Fort Worth final. Harold Solomon of the USA beat the Australian in the final of the 1977 Tournament of Champions WCT.

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#3 John McEnroe - 12

John McEnroe lost a total of 12 times in the finals of ATP 500 events over a 10-year period that began in 1979.

McEnroe's doubles partner Peter Fleming beat him in the title round in Los Angeles in 1979 while Vitas Gerulaitis and Bjorn Borg got past the American in the finals at Forest Hills and Stockholm in 1980.

Jimmy Connors won the bout against McEnroe at Queen's Club in 1982 while Ivan Lendl triumphed at San Francisco in 1983 and at Forest Hills in 1985.

McEnroe lost four ATP 500 finals in 1987. Tim Mayotte beat the American in Philadelphia before Stefan Edberg did the same in Rotterdam. Mats Wilander reigned supreme in Brussels while Lendl won at Stratton Mountain at McEnroe's expense.

Boris Becker beat his senior rival in the 1988 Indianapolis final before Lendl got past McEnroe in Montreal in 1989.

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#2 Ivan Lendl - 13

Between 1981 and 1993, Ivan Lendl was one of the best in the business, winning 24 ATP 500 titles while losing 13 finals.

The Czechoslovakian retired midway through his final against Yannick Noah in Richmond in 1981 before losing to Guillermo Vilas in Monte Carlo the following year. ATP 500 finals losses followed against Peter McNamara and Jimmy Connors in Brussels in 1983 and Rotterdam in 1984.

Connors continued to trouble Lendl, winning the Tokyo title in 1984 while John McEnroe beat the Czechoslovakian at Forest Hills the same year. McEnroe beat Lendl again in the Stratton Mountain final in 1985 before Boris Becker reigned supreme in Chicago in 1986.

McEnroe won the title round at Stratton Mountain again in 1987 before Stefan Edberg beat Lendl to triumph in Tokyo in 1991.

Lendl retired during the course of his last-ever ATP 500 final against Mark Woodforde in 1993.

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#1 Jimmy Connors - 18

Jimmy Connors won 109 tour titles and finished as the runner-up 55 times, losing a total of 18 ATP 500 finals.

Connors lost to Ilie Nastase in the final of the WCT Challenge Cup in 1976 which was followed by a defeat against Manuel Orantes at Indianapolis in 1977. Bjorn Borg got past the American legend in the final of the Pepsi Grand Slam in 1977, 1978, and 1979.

Borg dominated Connors during that period, also getting the better of his rival in the finals of the WCT Challenge Cup and Tokyo Indoor in 1979.

A legendary rivalry with John McEnroe was in its nascent stages as Connors lost the 1980 Memphis final while Peter McNamara prevailed over the American in Monte Carlo in 1981.

Guillermo Vilas won the Milan final against Connors in 1982 while McEnroe beat his senior compatriot in San Francisco the same year and yet again at Wembley in 1983.

Ivan Lendl began to assert his supremacy by defeating Connors at Rotterdam in 1984 and at Fort Myers the following year, while McEnroe won the Chicago tournament after Connors, who was then 32, failed to take the court owing to a torn muscle in his back.

Connors had to retire yet again midway through the Queen's Club final against Tim Mayotte in 1986 and did much the same at Milan in 1988 when he was up against Yannick Noah.