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Andy Murray and Rafael Nadal through at the Madrid Open, but Roger Federer falls to Nick Kyrgios

Andy Murray beat Philipp Kohlschreiber for the second time in three days to advance to the third round of the Madrid Open in a match that finished just before 3am local time.

The delayed match, which began at 1am, looked like it would be over quickly when Murray made a quick start but Kohlschreiber dug in to take it to three sets before tiredness took hold of the German.

Second seed Murray's 6-4 3-6 6-0 triumph came hot on the heels after he secured his first-ever clay title at Kohlschreiber's expense in Munich on Monday, but this was a clash that was made even harder by the fact it dragged out into the early hours of Thursday morning.

Top-seeded Roger Federer made an early exit in a thrilling second-round loss to Nick Kyrgios.

The 20-year-old Australian ended Federer's hopes of a fourth title at the Spanish tournament by rallying for a 6-7(2) 7-6(5) 7-6(12) victory.

Kyrgios is in form, having reached the final at the Portugal Open before losing to Richard Gasquet. The 2014 Wimbledon quarter-finalist also relinquished his status as the ATP's highest-ranked teenager by turning 20 last week.

Federer said his problem was that "I couldn't return his first serve. It was just a horrible performance on the return."

Kyrgios said he had been excited at the prospect of playing his childhood hero.

"Last night it was a bit tough to get some sleep," he said. "I've been playing well recently on the clay, so I knew I had a good chance to go out there and do well. I stuck to my game and served well and I got the win."

Clay king Rafael Nadal broke Steve Johnson's serve three times in a 6-4 6-3 win and is aiming to extend his streak of winning at least one European ATP World Tour clay court title in the run-up to Roland Garros to 11 consecutive years.

In other men's results, sixth-seeded Tomas Berdych beat Richard Gasquet 7-6(3) 7-5 and No.7 David Ferrer had a 6-4 6-0 win over fellow Spaniard Albert Ramos-Vinolas.

The 10th-seeded Grigor Dimitrov rallied for a 3-6 6-2 7-5 victory over Fabio Fognini, John Isner beat Thomaz Bellucci 7-6(5) 6-7(11) 6-1, Simone Bolelli had a 4-6 6-3 6-2 win over Luca Vanni in an all-Italian matchup, and Jo-Wilfried Tsonga ousted Jack Sock 6-3 1-6 7-6(4).