By Chris Oddo

(May 7, 2013) -- It took three hours, lots of anguish and a fair amount of self-doubt, but in the end Grigor Dimitrov notched the biggest win of his young career on Tuesday evening in Madrid.

The Bulgarian whipped up a stirring 7-6(6), 6-7(8), 6-3 victory over Novak Djokovic at the Mutua Madrid Open, his first ever triumph over a World No. 1, and his first win in ten tries against top 5 competition.

"I congratulate him," Djokovic said afterwards. "He played great tennis and he deserved to win."

In a battle lasting three hours and four minutes, Dimitrov saw a match point in the second set tiebreaker, but Djokovic stayed alive after a courageous serve and volley attempt ended with Dimitrov netting a backhand return.

Dimitrov, who hit 13 aces and saved 10 of 12 break points on the evening, ensured that Djokovic's Madrid campaign would end early when he fought off all three break points he faced in the decider after securing a service break in the first game of the set.

With the crowd chanting “Dimitrov, Dimitrov,” the Bulgarian made the sign of the cross on his chest before drawing the forehand error from Djokovic on his second match point of the evening at 3-5, 15-40.

"For the crowd, they picked him as the favorite player to support," Djokovic lamented, in a post-match press conference, "so that's all I can say."

Dimitrov then let loose tears of joy before signing the camera “I love you dad” after a hearty handshake with Djokovic at the net.

For Djokovic, who lost to his compatriot Janko Tipsarevic in the quarterfinals last year at Madrid, his earliest exit of the season might have come at the right time. Nursing a right ankle injury since his Davis Cup appearance in April, the Serb twisted the same ankle today during the second set, and needed to get medical attention before continuing.

Afterwards, Djokovic expressed relief that the injury didn't appear to be any worse off than it was before the tournament started. "Right now that is the only positive thing that I look into, is that I didn't injury my ankle worse before Rome and Paris," he said.

While Djokovic was struggling with his ankle in the second set, and playing what by all accounts was mediocre tennis by his standards, Dimitrov started to cramp. When the Bulgarian failed to convert his match point in the tiebreaker, his chances at pulling the shocker appeared to diminish drastically after Djokovic leveled the match and appeared to have all the momentum on his side of the court.

But Dimitrov found the will to push through, seizing the momentum back early in the final set, and finally closing the deal, much to the delight of what seemed to be a very anti-Djokovic crowd.

In suffering his third loss of the season, Djokovic drops to 26-3 on the season with three titles. He will maintain a comfortable hold on the No. 1 ranking regardless of the outcome in Madrid.

Dimitrov, a player who has long been considered one of the game's most promising, can now breathe a sigh of relief. He has put forth some sparkling performances this season, compiling a record of 16-9, but he has failed to find ways to achieve a signature victory – until today. After winning only one of his first 18 matches against the ATP's top ten (including blowing a big first-set lead against Djokovic several weeks ago in Indian Wells and another close call with Rafael Nadal in Monte Carlo), Dimitrov has won his last two in a span of three weeks.

The 21-year-old Bulgarian improved to 15-0 this season when winning the first set. He will face the winner of the Stan Wawrinka-Santiago Giraldo match in the third round.

Federer returns with a Win

Roger Federer played his first match since losing to Rafael Nadal at Indian Wells this March, defeating Radek Stepanek, 6-3, 6-3. "Yeah, pretty good," the defending champion said of his effort. "I didn't think I played incredible, but that's not what I was expecting myself to do here. But I didn't play bad, either. So I'm very happy with how things went today. Stepanek is also a player who can cause a lot of difficulties in the game. He doesn't look for rhythm necessarily."

Andy Murray also advanced, edging past German Florian Mayer in two tiebreaker sets, 7-6(11), 7-6(3).

(Photo Credit: AP)