Madrid: World No.1 Novak Djokovic was knocked out in the second round of the Madrid Masters after a 6-7 (6), 7-6 (8), 3-6 defeat to Bulgarian Grigor Dimitrov in a match lasting three hours and five minutes.
A tight, hard-fought first set was taken by Dimitrov in the tie-break and Djokovic looked to be heading out of the tournament late Tuesday night in the second set when Dimitrov broke his serve in the sixth game to take a 4-2 lead.
But the Serb broke back to take the set to another tie-break, which he won after 18 nerve-wracking points.
Dimitrov again broke Djokovic`s serve in the first game of the deciding set and held his own to take a 2-0 lead. The following games went with serve, but in the ninth game the Bulgarian broke Djokovic again to seal the biggest shock of the tournament to date.
Djokovic`s fellow countryman, Janko Tipsarevic was the victim of another upset as he lost 6-7 (5), 3-6 to Argentine Juan Monaco. The No.9 seed crashed out in just over an hour and 41 minutes.
Andy Murray also suffered in his match against German Florian Meyer, although the Scot eventually emerged triumphant.
The World No.3 won a marathon first set 7-6 after a 21 point tie-break during which he had to defend several set points against him.
Meyer then raced into a 4-1 lead in the second set, before Murray again showed his battling qualities to level 5-5 and then 6-6 to take the second set to another tie-break.
This time Murray wasted no time in the tie-break and quickly found himself with four match points and although Meyer was able to save the first, Murray won the next point to grab the set and take the match 7-6 (11), 7-6 (3).
In contrast to Djokovic and Murray, reigning champion Roger Federer enjoyed a comfortable ride into the third round of the Madrid Masters with a straight 6-3, 6-3 win over Radek Stapanek.