For the sixth time, Novak Djokovic played for the first-place prize in Cincinnati as he tried to become a titleholder at all the Masters events in his career.

He would succeed over a formidable foe in Roger Federer, 6-4, 6-4, to capture his 31st ATP Masters 1000. He's the first player in the 28-year history of the Masters to win all nine events.

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His bid for history had some resemblance to the past results of some of the ATP and WTA’s all-time greats, who were also missing one piece of the puzzle to complete a set. It’s never an easy task, a fact these players can attest to.

Here’s a look at several players who missed the opportunity to fill a hole in their legendary resumes.

1

The Bryan brothers’ Calendar Slam bid ends…

By the time 2013 rolled around, Bob and Mike Bryan had accomplished nearly everything on the doubles court. The only thing missing was a calendar-year Grand Slam, and they took that mission head-on that year, winning the first three majors. At the US Open, though, their streak was stopped in the semifinals by Leander Paes and Radek Stepanek in three sets.

2

…And so does Serena’s

Having completed the second “Serena Slam” of her career after Wimbledon 2015, Williams was on the verge of becoming the first singles player in nearly 30 years to win all four majors in a season going into the US Open. In the semis, her march toward history was stopped by Roberta Vinci in one of the game’s biggest upset.

3

McEnroe misses out on the French

In 1984, John McEnroe started off the year perfectly with seven titles on the trot. He advanced to his first French Open final to face Ivan Lendl, who had lost his four previous Grand Slam championship matches. McEnroe quickly went up two sets to none, but lost his way and Lendl rallied for the five-set win. He would never advance that far at Roland Garros again.

4

Lendl misses out on Wimbledon

Though Lendl was the world’s most dominant player for years, he could never conquer the one tournament that grew to be the most important to him, Wimbledon. At the time, serving and volleying was the key to success and he made himself a capable one. The only thing was there were players who could do it better, such as Boris Becker, who beat him in the 1986 final, and Pat Cash, who got him in 1987.

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5

A double fault does in Becker’s clay-court hopes

Succeeding on a surface that doesn’t play to your strengths is a tough feat to pull off. Lendl had to overcome his natural tendencies on grass and one of his chief rivals, Becker, had to do it on clay. The German did have some success, with some French Open semifinals and a few finals. His best opportunity came in the 1995 Monte Carlo final, where he faced two-time champ Thomas Muster. Becker went up two sets to none before Muster rallied for the win, helped in large part by a risky double fault from Becker, who was up match point.

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