From time to time, the difficulty of winning an ATP Masters 1000 tournament is compared to the difficulty of winning a Grand Slam tournament. This is because of how Masters events are scheduled. Masters champions must win a Friday quarterfinal, a Saturday semifinal, and a Sunday final—sometimes after playing on Thursday. Unseeded players who manage to navigate through the stacked draws are often asked to win six matches in seven days, if not six in six (which Julien Benneteau must do if he’s to win Cincinnati this week). Grand Slams, on the other hand, ask its champions to win seven matches over a two-week stretch.

But despite the taxing itineraries at the Masters, the best-of-five-set versus best-of-three-set format almost always tilts the argument in favor of the Slams.

Here’s a question, though: Is it harder to win a career Grand Slam, or, as the ATP has put it on Twitter, a Career Golden Masters?

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That’s a trickier comparison, especially when you consider that seven men have won all four major titles (Fred Perry, Don Budge, Rod Laver, Roy Emerson, Andre Agassi, Roger Federer, and Rafael Nadal)—and no one has won all nine ATP Masters tournaments. The “Masters” concept wasn’t born until 1990, true, but the “zero” is an elephant in the room. There are cases to be made for both career achievements.

Perhaps Novak Djokovic is in the best position to answer—the Serb is one title short of completing both checklists. Despite his best efforts, the French Open has eluded him, and so has the Cincinnati Masters. That will remain so until at least 2015, as Djokovic’s quest to become Cincy champion ended today, at the hands of 16th-seeded Tommy Robredo, 7-6 (6), 7-5.

It’s not like Djokovic hasn’t given it his best shot in Ohio before. He’s a four-time finalist at what is currently called the Western & Southern Open, and hard courts are largely considered his best surface. But the Cincy curse lives on. The world No. 1 looked out of sorts against Robredo, much like he’s appeared to be since Wimbledon, and his subsequent wedding. This match was not as close as the scores indicated; Robredo should have won the second set 6-4, but tensed up on two match points. When he got a third chance, he didn’t let it slip away:

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A few more tweets of note about Djokovic’s latest loss, which follows last week’s round-of-16 loss to Jo-Wilfried Tsonga in Toronto (Steve Tignor will give his thoughts in tomorrow’s First Ball In):

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