On October 18, 2008, Andy Murray defeated Roger Federer 3-6, 6-3, 7-5 in the Madrid semi-final for his second straight Masters 1000 final after Cincinnati. The Briton lost the first four Masters 1000 semi-finals. He changed that in Cincinnati 2008 when he defeated Ivo Karlovic before prevailing over Novak Djokovic for the first crown at that level.
Two months later, Andy secured a place in another Masters 1000 final in Madrid, overcoming world no. 2 and the 2006 champion and the last year's finalist Roger Federer. It was only the fifth meeting between Murray and Federer, considering their first clash came in Bangkok three years earlier.
The Briton scored the third victory thanks to a better performance in the closing stages, rattling off the last three games to advance into the title clash against Gilles Simon. The youngster delivered fury from the initial shot, blasting 14 aces and taking 85% of the points on the first serve.
He fended off two out of three break chances to keep the pressure on Roger. The Swiss grabbed that break in the first set and had to dig deep in his games, fending off seven out of nine break chances and failing to match the rival's numbers.
Andy had more winners, fewer unforced errors and more mistakes forced, overpowering Roger in the shortest rallies and staying in touch in the more extended ones to remain on the title course. They needed 12 minutes to complete the opening five games with a rock-solid performance from the servers.
Roger forced Andy's error to forge a break chance at 3-2. Murray repelled it but could not do the same with the next one, spraying a forehand mistake to suffer a break and push Federer 4-2 in front.
Andy Murray toppled Roger Federer in three sets to reach the 2008 Madrid final.
The Swiss fended off a break chance in the next one with a service winner.
He closed the game with another to cement the advantage and wrapped up the opening set with a hold at love at 5-3 after just 31 minutes. The Briton had to find something extra on the return in set number two to stay in contention.
He did that in game four, taming the rival's serve and scoring a break with a well-constructed attack that sent him 3-1 up. Murray confirmed the lead with a backhand winner and delivered another comfortable hold to move 5-2 in front.
The Briton clinched the set with three winners in the ninth game to send the encounter into a decider. Andy stepped in from set number two, taking the ball early and dropping only four points behind the initial shot, ready for more of that in the encounter's final part.
Still, Federer struck first after Murray's loose volley in the second game. He created a break chance that Andy fended off with a quick attack to keep his serve intact. The Briton gathered momentum and created three opportunities on the return in the next game.
Federer erased them with three winners, brought the game home and picked a massive boost ahead of the return game that could have proved problematic for Andy. Instead, Murray landed four service winners to level the score at 2-2 and earned a break chance in the next one.
He wasted it when his backhand landed long but stayed on the right track after four more winners in game six that kept him safe at 3-3. Federer held with ease in the seventh game and created a 30-0 lead on the return in the next one, missing a forehand that could have given him two break chances!
Andy closed the game to remain on the positive side and locked the result at 5-5 after an ace in game ten. The Swiss sent a forehand wide in the 11th game to offer his opponent two break opportunities. Roger saved them before Andy converted the third after forcing an error from world no.
2. The Briton gained the advantage and sealed the deal when Federer netted a backhand in game 12 to advance into his second straight Masters 1000 final. This defeat ruined Roger's chances of finishing as the year-end no. 1 for the fifth consecutive year, allowing Rafael Nadal to take the honor despite losing an epic clash against Gilles Simon on the same day.