[7] This is the reason he cites Michael Chang as a major influence, as his comparatively small frame proved that size was not the only factor in playing tennis.

The Frenchman reached his first ATP Tour final in Valencia with wins over Andreas Seppi in the quarterfinal and Fernando Verdasco in the semifinal, but lost to Nicolás Almagro.

After his third-round loss to fellow French Richard Gasquet at Wimbledon, Simon left Europe for the United States to familiarize himself with the hardcourts before the US Open Series.

Simon participated in the 2008 Summer Olympics in Beijing, playing in the singles for France alongside Paul-Henri Mathieu, Michaël Llodra, and Gaël Monfils.

On day six, he lost in the third round to the 17th seed Juan Martín del Potro, in a five-set match that lasted 3 hours and 47 minutes.

[10] By the end of 2008, France had four players in the top 20 (Simon, Tsonga, Gasquet, and Monfils), for the first time since computer rankings were established in 1973.

[11] On 3 November, he qualified for the Tennis Masters Cup, a tournament usually reserved for the world's top eight players in Shanghai, after Rafael Nadal withdrew due to knee complications and fatigue.

6 and played at the Hopman Cup, teaming up with compatriot Alizé Cornet to form the French mixed doubles duo.

He participated in the Davis Cup with other French team members Michaël Llodra, Jo-Wilfried Tsonga, and Richard Gasquet.

Simon lost to Tomáš Berdych, and then played Radek Štěpánek (whom his fellow team member Tsonga beat).

[citation needed] At Wimbledon, Simon reached the fourth round where he lost to unseeded Spaniard Juan Carlos Ferrero.

One week later, he played at the Cincinnati Open where he defeated Nikolay Davydenko en route to the quarterfinals, where he would lose to world No.

At the 2009 US Open, Simon equalled his best result of third round before retiring with a right knee injury during his third-round match against Juan Carlos Ferrero.

Although with his movement severely hampered, Simon decided to play on to finish the match in front of an enthusiastic home crowd.

The injury eventually caused Simon to miss the entire spring European clay-court season, including the French Open.

However, he suffered first-round defeats in his next two ATP Masters 1000 tournaments, the Rogers Cup in Toronto and the Western & Southern Open in Cincinnati.

The next tournament was the Valencia Open 500, where Simon beat two seeds (Fernando Verdasco and Nikolay Davydenko) en route to his semifinal appearance, only to lose to the Spanish qualifier Marcel Granollers.

But day 3 opened with Djokovic in strong form defeating Monfils in three easy sets, leaving the championship to a deciding fifth match.

France's defeat caused some to question the choice of Llodra to play Troicki when Simon has a 4–0 head-to-head record against the Serb.

One week later, he beat Alexandr Dolgopolov and Ernests Gulbis in the quarterfinals and semifinals and then captured his eighth title by defeating Viktor Troicki, in the final of the Sydney International.

At the US Open, he advanced to the fourth round by defeating Ricardo Mello, Guillermo García López, and Juan Martín del Potro before losing to John Isner.

[25] In September, he won the Moselle Open for his 11th career title, beating Jo-Wilfried Tsonga in the final, in straight sets.

He lost to Tsonga in the third round of the 2014 Australian Open after beating both Daniel Brands (saved seven match points) and Marin Čilić in five sets.

Simon reached the final of the Shanghai Masters, upsetting Stan Wawrinka, Tomáš Berdych and Feliciano López.

5, Simon lost in the first round of the World Tour 250 Series event in Brisbane to unseeded Grigor Dimitrov to start the year.

At the Australian Open, he was forced to retire from his second-round match when he was trailing 2–6, 0–3 against the tenth seed Pablo Carreño Busta because of an injury to his left thigh muscles that he had sustained the week before in Sydney.

[28] Simon won his 14th ATP Tour singles title of his career in Metz, defeating Matthias Bachinger in the final.

This event normally took place in Cincinnati, Ohio, but was held at the USTA Billie Jean King National Tennis Center in New York City, in order to reduce unnecessary player travel by centralizing the tournament and the subsequent US Open in the same venue.

[68] After suffering that first-round defeat, he announced that he would be stepping away from the tour for an undetermined period of time because his heart wasn't in it and also for his mental health.

[94] It was his 300th hard court win in his career, making him the 24th man to reach that milestone in the Open Era, and just the ninth active men's player.