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Novak Djokovic lost all three matches at his ATP Finals debut in 2007. Novak returned to Shanghai a year later and rose to stand among the favorites. It was the last ATP Finals edition in Shanghai, and Djokovic made sure to turn it into a memorable one.
Novak's first victory at this event came against Juan Martin del Potro. The Serb toppled Nikolay Davydenko to secure a place in the semi-final despite losing the last round-robin clash to Jo-Wilfried Tsonga. Djokovic faced another Frenchman in a battle for the final and had to give 120% to prevail and remain on the title course.
Novak overpowered Gilles Simon 4-6, 6-3, 7-5 in a grueling two hours and 52 minutes for his first ATP Finals title clash. It was Djokovic's first win over Simon, and he had to work hard to earn it. The Serb won 11 points more, delivering better numbers behind the second serve and fending off six out of eight break chances.
Novak converted three out of 14 return opportunities, taking the last two games at 5-5 in the decider to advance and set a Nikolay Davydenko clash. Djokovic was a more aggressive player. He hit around 40 winners and 55 unforced errors and forced 45 Simon's mistakes to find a way toward the finish line.
The persistent Frenchman secured a break in the encounter's third game after causing the Serb's error. Gilles confirmed the advantage with a hold in the next one after a forehand down the line winner for 3-1. Serving well, Simon opened a 5-3 lead with a service winner and wasted four set points on the return in game nine.
Novak Djokovic prevailed over Gilles Simon at the 2008 ATP Finals.
Novak survived that game, but Gilles remained focused and delivered a hold at 30 at 5-4 to wrap up the opener and move a set away from the final on his debut.
The Frenchman received a medical timeout on his neck after the second set's third game and got broken in the next one to fall 3-1 down. Serving for the set at 5-3, Djokovic blasted a service winner to wrap it up and bring a decider.
Novak grabbed a couple of incredible rallies and became the favorite ahead of the final set. Novak wasted a break chance in the early stages. He fixed that two games later when he grabbed a break following Gilles' forehand error at the net.
Returning at 3-1, Djokovic wasted four break opportunities that could have sent him closer to the finish line. He underwent treatment on his left leg during the break and continued with solid serving. Simon held at love in the ninth game to prolong the match, and Djokovic served for the victory in the next one.
Gilles refused to surrender and broke back to level the score at 5-5 following Novak's costly double fault. The Serb remained calm and clinched another break in game 11 to build the advantage. Djokovic sealed the deal with a perfect drop shot at 6-5 to celebrate victory and move into the final.