Ben Shelton and Brandon Nakashima are set to contest the Canadian Open final on Wednesday.
Shelton, the world number 10, is looking to win back-to-back titles in the North American nation.
Meanwhile, Nakashima will be hoping to claim his first Masters title.
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The winner of Wednesday’s contest will then travel to the Cincinnati Open, seeking to become only the seventh man in the Open Era to win the Canadian Open and Cincinnati Open in the same calendar year.
Six have accomplished the feat since 1968; who are they?
Cliff Richey
Richey, the former world number six, became the first man to win the Canadian Open and Cincinnati Open in the same year [during the Open Era] when he triumphed at both events in 1969.
The American began his North American campaign by beating compatriot Butch Buchholz in the Canadian Open final, winning 6–4, 5–7, 6–4, 6–0.
Richey also overcame the challenge of Australian Allan Stone in the Cincinnati Open final, triumphing 6–1, 6–2.
Richey did not win another title at either event after 1969.
Eddie Dibbs
Another American accomplished the feat in 1978.
Eddie Dibbs, a Roland Garros semi-finalist who was born in Brooklyn, New York, defeated José Luis Clerc in the 1978 Canadian Open final.
Dibbs, who beat Clerc 5–7, 6–4, 6–1, also captured his first title in Cincinnati that very same year.
The former world number five beat Mexican Raul Ramirez in the championship match, 5–7, 6–3, 6–2.
Andre Agassi
Agassi is one of the most iconic figures in tennis history.
The American star won eight Grand Slam titles during his tumultuous career, also achieving the world number one ranking.
Agassi also won the Canadian Open and Cincinnati Open in 1995.
Agassi first beat Pete Sampras in the Canadian final, winning 3–6, 6–2, 6–3.
He then triumphed in Ohio, securing a 7–5, 6–2 victory over Michael Chang in the final.
Pat Rafter
Rafter, a two-time US Open champion, secured back-to-back titles in 1998 by triumphing in Canada and Cincinnati.
Rafter, from Australia, defeated former Wimbledon champion Richard Krajicek in the Canadian Open final, triumphing 7–6, 6–4.
He later defeated Pete Sampras in the Cincinnati showpiece event, winning 1–6, 7–6, 6–4.
Rafter went on to capture his second consecutive US Open title later that year, beating Mark Philippoussis in the final.
Andy Roddick
A fourth American wrote his name into the history books only eight years after Agassi’s successes in North America.
Andy Roddick won the Canadian Open and Cincinnati Open in 2003, beating David Nalbandian and Mardy Fish in the respective finals.
Roddick secured the world number one ranking for the first time following his victory against Fish.
Later that summer, Roddick won his one and only Grand Slam title at the US Open.
“I knew I was going to cry,” said Roddick after beating Juan Carlos Ferrero 6-3 7-6 6-3 in New York. “I was just so happy and wanted to share the moment with everyone who has supported me.
“I have my friends and my family here, everyone I know is here supporting me and I couldn’t have a better day.”
Rafael Nadal
Nadal, a 22-time major champion, is the second-most successful player in Canadian Open Men’s Singles history.
The Spaniard won five titles during his career, trailing only Ivan Lendl, who won six.
The third of Nadal’s five Canadian Open titles was won in 2013. The 14-time Roland Garros champion beat Milos Raonic in the final, 6–2, 6–2.
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Nadal then travelled to Cincinnati, where he claimed his one and only Cincinnati Open crown.
Nadal beat John Isner in the final, winning 7–6, 7–6.
The Spanish superstar claimed his second US Open title later that year, beating Novak Djokovic in the final.
