The last player to win the Canadian Open and Cincinnati Open back-to-back as Ben Shelton loses in the quarterfinals

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Ben Shelton’s bid to win back-to-back Masters 1000 titles came to an abrupt end in the quarterfinals.

In Toronto, Shelton beat Karen Khachanov to win the Canadian Open title.

Returning to action in Cincinnati, the 22-year-old was searching for his second consecutive title and started well, defeating Camilo Ugo Carabelli, Roberto Bautista Agut, and Jiri Lehecka in straight sets to reach the quarterfinals.

Unfortunately for the world number six, it was in the quarterfinals that his run came to an end, as Shelton lost to Alexander Zverev 2-6, 2-6.

Failing to win the Canadian Open and Cincinnati Open in the same year, Shelton joined the long list of ATP stars who came up short.

In fact, since the Masters series was first introduced in 1990, just three players have accomplished the remarkable feat.

Andre Agassi in 1995, Andy Roddick in 2003, and another multiple-time Grand Slam champion in 2013.

Rafael Nadal won both the Canadian Open and Cincinnati Open in 2013

12 years ago, Spain’s Rafael Nadal travelled to Montreal as the number-four seed, looking to pick up his third Canadian Open title.

Making light work of his first three opponents, Nadal set up a scintillating semifinal clash with the number-one seed, Novak Djokovic.

• 2013 Canadian Open 2R – Rafael Nadal beat Jesse Levine, 6-2, 6-0
• 2013 Canadian Open 3R – Rafael Nadal beat Jerzy Janowicz, 7-6, 6-4
• 2013 Canadian Open QF – Rafael Nadal beat Marinko Matosevic, 6-2, 6-4

In a match best remembered for a heated moment during the third set, Nadal won 6-4, 3-6, 7-6.

Moving on to play home-favorite Milos Raonic in the final, Nadal secured the win in style, winning 6-2, 6-2.

Heading south to Cincinnati, Nadal encountered one of his biggest rivals in the quarterfinals but again won in a deciding set, as he qualified for the final.

• 2013 Cincinnati Open 2R – Rafael Nadal beat Benjamin Becker, 6-2, 6-2
• 2013 Cincinnati Open 3R – Rafael Nadal beat Grigor Dimitrov, 6-2, 5-7, 6-2
• 2013 Cincinnati Open QF – Rafael Nadal beat Roger Federer, 5-7, 6-4, 6-3
• 2013 Cincinnati Open SF – Rafael Nadal beat Tomas Berdych, 7-5, 7-6

After playing Canada’s Raonic in the Montreal final, Nadal now had to play America’s John Isner in the Cincinnati final.

Lucky for the Spaniard, by 2013, he was as popular as any hometown star could be, so didn’t have much trouble getting the crowd on side.

Winning two tiebreakers, 7-6 [10-8], 7-6 [7-3] Nadal became just the third player in the Masters era to win the Canadian Open and Cincinnati Open titles in the same year.

Asked about the accomplishment in his post-match press conference, Nadal explained why it’s so hard to win back-to-back Masters tournaments.

“It’s very difficult to win a Masters 1000,” he said.

“We play from the first round against the best players in the world, top 50 players in the world. In other kinds of tournaments, you can have good draws. Here, you cannot have good draws.

“Winning back‑to‑back tournaments is, first of all, difficult because, first thing, the courts are not exactly the same. The weather conditions are not exactly the same. The rivals bring your body and your tennis to the limit

“I was lucky. I was close to losing against Roger [Federer] the other day. I was close to losing against Novak [Djokovic] in Montreal. I was close today. So I was able to save a few matches that were very, very close.”

Perhaps unsurprisingly, no player has won both tournaments in the same year since, but has anyone come close?

How have Canadian Open champions performed at the Cincinnati Open since 2013?

Since Nadal won both tournaments in 2013, no player has qualified for the Cincinnati Open final after winning in Canada.

Perhaps more remarkably, five of the eight players who chose to compete in Cincinnati after winning in Canada lost their opening match.

Winning the Canada/Cincinnati double continues to be one of the trickiest tasks in all of tennis.

Only time will tell if we will see another player join Agassi, Roddick, and Nadal in winning both tournaments in the same year, but it will certainly be something to look out for in 2026.