On October 18, 2008, Andy Murray defeated Roger Federer 3-6, 6-3, 7-5 in Madrid semi-final, advancing into the second straight Masters 1000 final after Cincinnati. The Briton had lost the first four Masters 1000 semi-finals, which changed in Cincinnati 2008 when he defeated Ivo Karlovic before prevailing against 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, fending 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 in the end. Thus, Roger missed the opportunity to reach the third straight final in Madrid and fight for the last indoor title at this event before it switched to clay from 2009.
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 seal the deal and remain on the title course. They needed 12 minutes to complete the opening five games with a rock-solid performance from the servers before Roger forced an error from Andy to forge a break chance at 3-2.
Murray repelled that one but couldn't do the same with the next, spraying a forehand mistake to suffer a break and push Roger 4-2 in front.
In Madrid 2008, Andy Murray toppled Roger Federer in three sets to reach the final.
The Swiss fended off a break chance in the next one with a service winner, closing the game with another to cement the advantage and wrapping 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 and 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 break with a backhand winner, delivering another comfortable hold to move 5-2 in front and clinching the set with three winners in the ninth game to send the encounter into a decider. The Briton 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 final part of the clash.
Still, Federer was the one who made the first strike after a loose volley from Murray in the second game, creating a break chance that Andy fended off with a quick attack, gathering momentum and creating three opportunities on the return in the very next game.
Federer erased those with three winners, bringing the game home and picking a massive boost ahead of the return game that could have proved to be problematic for Andy after all the possibilities he squandered. Instead of that, Murray landed four service winners to level the score at 2-2 and earned a break chance in the next one, wasting it when his backhand landed long but staying 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, missing a forehand that could have given him two break chances! In the end, Andy closed the game to remain on the positive side of the scoreboard and locked the result at 5-5 after an ace in game ten, switching the pressure back to Roger's part of the net.
The Swiss sent a forehand wide in that 11th game to offer his opponent two opportunities for a break, saving those 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 the 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 for the first time despite losing an epic clash against Gilles Simon on the same day.