Making his Masters Cup debut in 2002, Roger Federer would win his first encounter in the first five trips to the premium ATP event. With three matches to determine the semi-finalists, a player is keen to make a winning start and get himself in a good position ahead of the remaining two clashes, which wasn't always the case.
Following those five consecutive first-match triumphs, Roger suffered a defeat at the beginning of the 2007 campaign, finding himself on the losing side against Fernando Gonzalez in a thriller. A year later, the Swiss had to work from a win down again, as Gilles Simon toppled him 4-6, 6-4, 6-3 in two hours and eight minutes.
It was their second duel of the season and the Frenchman's second victory, both after losing the opening set. Simon won three ATP titles that season, securing the Masters Cup berth when world no. 1 Rafael Nadal withdrew due to an injury, getting a chance to make a dream debut against Roger Federer.
For the first time in five years, Federer wouldn't finish as the year-end no. 1 player, losing the ATP throne to Rafa in August and not competing on the same level as in the previous four seasons. Simon claimed eight points more than Federer, drawing more from his second serve and prevailing in the crucial moments to secure one of his career-best victories.
The Frenchman saved eight out of ten break chances, delivering three breaks from 12 opportunities to seal the deal and make a winning start. Roger added his name on the scoreboard with a forehand winner in the second game and wasted his opportunities for an early lead in the next one.
In 2008, Gilles Simon defeated Roger Federer twice from as many matches.
The Swiss endured a lengthy rally in game five and grabbed a break with a forehand winner that sent him 3-2 in front. Serving for the opener at 5-4, the four-time champion placed a service winner down the T line, looking good so far and hoping for more in set number two.
Gilles was in all kinds of trouble after getting broken in the second set's third game, staying calm and pulling the break back a few minutes later after forcing an error from Roger. World no. 2 created a break chance at 3-3 with a smash winner that could have carried him home, denied by Simon, who closed the game to remain 4-3 in front.
The eighth game brought drama and excitement, with Federer fending off break opportunities to stay in touch, hoping for a late break that would carry him home. The Frenchman closed the ninth game with a volley winner and secured a break with another great point at the net a few minutes later to steal the set 6-4 and force a decider.
Ready to fight, Roger escaped from 40-0 down on serve in the sixth game of the final set, earning three break chances in the next one that could have pushed him closer to the finish line. Producing some incredible shots, Simon survived and stayed unbroken before delivering a crucial break with a forehand winner that sent him 5-3 up.
Serving for the victory, Gilles held at 15 with an ace down the T line to seal the deal and make a winning start of his first Masters Cup campaign, beating Roger for the second time in as many encounters.