Grigor Dimitrov stunned Novak Djokovic in the second round of the Madrid Open on Tuesday, beating the top-ranked Serb 7-6 (6), 6-7 (8), 6-3 for the biggest win of his career.

The 28-ranked Bulgarian saved three set points in the first set before taking the lead, and Djokovic then appeared to hurt his right ankle when trailing 4-2 in the second. The Serbian player slipped on the baseline and winced in pain, then immediately called for a trainer and took a lengthy break to get treatment.

Crowd support

The wait for the game to resume annoyed the crowd, who turned against Djokovic and began chanting Dimitrov’s name.

Djokovic who ended Rafael Nadal’s eight-year winning streak at the Monte Carlo Masters last month said the loss had more to do with poor preparations than an injury.

Djokovic said: “I didn’t prepare myself so good. For 12 days after Monte Carlo, I haven’t touched the racquet.”

Djokovic said he didn’t understand why the crowd turned against him during the injury break. “I don’t see any reason for that. I didn’t do anything bad,” he said.

The crowd then displayed sympathy for Dimitrov when he appeared to suffer from cramps at 5-5 with the game at deuce, visibly upsetting the Serb.

Federer cruises

Earlier, defending champion Roger Federer looked comfortable on clay in his first match in two months, easing past Radek Stepanek of the Czech Republic 6-3, 6-3 to reach the third round.

The second-ranked Federer took a break after losing in the Indian Wells quarterfinals on hard court to Nadal, but instantly took to the slower red surface and broke early to take control of the first set.

Federer can equal John McEnroe’s career tally of 77 titles if he defends the Madrid trophy, having won last year on the heavily criticized blue clay that organisers decided to get rid of for this tournament. Like many of his fellow players, Federer said the traditional red surface was better.

Third-seeded Andy Murray had a tougher time against Florian Mayer before outlasting the German 7-6 (11), 7-6 (3).

Murray said he struggled with the altitude and found it hard to breathe at the end of the first set where “there were so many long points.”

No. 13 Tommy Haas and No. 15 Stanislas Wawrinka were among other seeded players to advance, while Richard Gasquet ranked no. 8 lost 7-5, 3-6, 6-4 to Daniel Gimeno-Traver of Spain.

In the women’s event, defending champion Serena Williams moved her title defense into the third round after beating Lourdes Dominguez Lino of Spain 6-2, 7-5.

The top-ranked Williams struggled a bit to counter her opponent’s drop-shots and lobs but stayed on course for a fourth title of the year and the 50th of her career.

Also, Marion Bartoli of France overcame a fall to beat qualifier Maria-Teresa Torro-Flor of Spain 6-4, 2-6, 6-4.

s

More In: Tennis | Sport