2008: First Grand Slam appearances In the first months of the 2008 season, Gil competed exclusively in the Challenger Tour. He reached the doubles final in Napoli in March. The next month, Gil was called up for the Portugal Davis Cup team to face Tunisia and won his singles match against Malek Jaziri. Then, he entered his first ATP Tour of the season at the Estoril Open where he reached the quarterfinals for the second time, after wins over Nicolas Mahut and João Sousa. He lost at that stage in straight sets to then world no. 1 Roger Federer. After a return to the Challenger Tour, during which he won his first Challenger doubles title in Marrakech, Gil made his Grand Slam main draw debut at the French Open. Following a successful participation in the qualifying rounds, he lost in the first round to Jérémy Chardy. In June, Gil won the Challenger singles title in Sassuolo and entered the Wimbledon Championships. Similarly to the French Open, he made it to the main draw through the qualifying rounds and was defeated by Chardy in the first round. Gil also entered the doubles event and reached the second round, partnering Dick Norman. Between July and August, Gil won another Challenger singles title in Istanbul and a doubles title in Turin. Also, he won all his three matches for Portugal Davis Cup team against Cyprus. In consequence, Gil became the second Portuguese player after Nuno Marques to enter the ATP top 100 singles ranking, and equaled Marques' world no. 86 career-high position. Gil then entered directly in the main draw of the US Open, where he lost again to Chardy in the first round. Gil played Challenger tournaments the remaining season, without reaching any finals. Despite the several milestones achieved during 2008, Gil finished the year ranked outside the top 100, at world no. 110. 2009: ATP World Tour breakthrough After skipping the Australian Open, Gil began his 2009 season with back-to-back semifinals appearances in ATP World Tour tournaments. At the SA Tennis Open, he defeated Guillermo García-López to become the second Portuguese to reach the semifinals at this level, after his coach João Cunha e Silva in 1992. Gil was defeated then by Jo-Wilfried Tsonga. At the Brasil Open, and after beating world no. 18 and reigning champion Nicolás Almagro, Gil lost in the semifinals to Thomaz Bellucci. In result, he broke