By Courtney Nguyen
May 07, 2013

Grigor Dimitrov Grigor Dimitrov picked up the biggest victory of his career on Tuesday. (Julian Finney/AP).

Grigor Dimitrov stunned top-ranked Novak Djokovic 7-6 (6), 6-7 (8), 6-3 on Tuesday in the second round of the Madrid Open. It was a dramatic three-hour, five-minute match that featured a hostile crowd, injury woes and cramping that looked like it might derail Dimitrov's upset bid.

Three thoughts on the young Bulgarian's breakthrough win in the ATP Tour's longest three-setter of the year.

1. It's been a long time coming. The debate surrounding Dimitrov over the years was whether he had substance to back up his style. It feels like we've been waiting for the 21-year-old to make his mark on tour ever since he won the junior titles at Wimbledon and the U.S. Open in 2008. But this is really the first year that Dimitrov has showed that he might just live up to all of the hype that came with being given (or cursed with) the "Baby Federer" nickname.

His results have improved after leaving the Mouratoglou Academy for Sweden's Good to Great Academy in December. He made his first ATP final in January, losing to Andy Murray in two tight sets at the Brisbane International. He also served for the first set against Djokovic at the BNP Paribas Open and against Murray at the Sony Open only to throw in multiple double faults and fail to convert. Then in Monte Carlo a few weeks ago he took a set off Rafael Nadal -- Rafael Nadal! In Monte Carlo! -- before losing in the quarterfinals.

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So the stage was set for Dimitrov to at least challenge Djokovic, who was playing his first match since beating Nadal in the Monte Carlo final 16 days ago. At first, it looked like a redux of their Indian Wells showdown, with Dimitrov once again serving for the first set only to be broken with relative ease. Djokovic was poised to run away with the tiebreaker after building a 4-1 lead, but Dimitrov stormed back with some clutch serving and benefited from a few loose errors from Djokovic to save two set points and win the breaker 8-6.

Things got dramatic in the second set. Down 2-4 but with a chance to break, Djokovic rolled his right ankle (the same ankle he injured last month in a Davis Cup tie against the United States) and looked to be in severe pain before taking a medical timeout to get it re-taped. He was able to secure the break when play resumed, and then it was Dimitrov's turn to feel the physical toll of the match. His fitness has been a question mark throughout his career and sure enough he began to cramp late in the second set. After Dimitrov lost the second-set tiebreaker 10-8, the conventional wisdom was that he was done and dusted. He's never shown the physical and mental resiliency to pull off a three-set win like this.

But Djokovic came out flat in the third and Dimitrov took advantage immediately by breaking the Serb in the first game. Dimitrov went on to hold serve throughout the set and then broke Djokovic again to complete the biggest win of his career. In tears after the match, Dimitrov wrote, "I love you dad" on the camera and soaked in the crowd's adulation. In a week in which 22-year-old Milos Raonic was upset in his opening second-round match and 20-year-old Bernard Tomic was embroiled in some unfortunate controversy, it was good to see a youngster step up with a big performance.

2. Don't read too much into Djokovic's performance. His inability to shut the door on a limping Dimitrov to start the third set was a shocker, but Djokovic says he didn't touch a racket for 12 days after the Monte Carlo in order to rest and heal his ankle. He also had to use an inordinate amount of energy to deal with the hostile Madrid crowd, which clearly took delight in his mistakes from the beginning. Yes, Djokovic yelled a Serbian expletive its way after he won the second-set tiebreaker after being whistled at following his ankle injury, with the fans possibly believing it was an act of gamesmanship. Then they booed him off the court after the loss.

"[Djokjovic] not talking much about the crowd, just said he doesn't understand why they were so hostile," one reporter tweeted after the match.

Given his lack of preparation and the unique conditions in Madrid -- a newly laid court and the altitude -- it's hard to read into this result in any meaningful way. This is not the Djokovic we will see in Rome or Paris.

"Very happy for young Dimitrov, such a charismatic player to watch!" ATP commentator Rob Koenig tweeted. "But in all honesty, Djokovic was at 65% this evening."

3. Let's hold off on the ticker-tape parade for Grigor: This was a big win for Dimitrov -- he becomes the first of the 22-and-under group to beat the original Big Three of Djokovic, Nadal and Roger Federer -- but it was just one win. It's still alarming that he's cramping in the second set of a match and this isn't the first time this has happened. He cramped against Nadal in Monte Carlo and against Richard Gasquet last year at Roland Garros. He needs to get physically stronger if he's going to compete at the Slams and have deep runs at ATP events. But the best thing about Tuesday's win is that Dimitrov showed everyone, including himself, that he can gut out a victory when he's physically compromised. This was as much a psychological win as a physical one.

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