loss at the Vienna Open and qualifying round exits at the Swiss Indoors and the Paris Masters. Despite his struggles to move past early rounds at ATP Tour level events in the second half of the season, Gil achieved a career high year-end ranking of 69 – the best season-ending ranking for a Portuguese player, which surpassed Nuno Marques' record world no. 92 in 1995 and lasted until Rui Machado broke it in 2011. 2010: Estoril Open singles runner-up Gil began 2010 season with first round exits at the Qatar Open and the Sydney International, both times against Potito Starace. Making his main draw debut at the Australian Open, Gil retired during a first round match against David Ferrer, when was trailing 6–0, 6–0, 2–0. In the doubles event, he partnered with Kristof Vliegen and went out in the first round as well. Gil's early round struggles continued at the Brasil Open, the ATP Buenos Aires, the Mexican Open and the Indian Wells Masters. Before Indian Wells, Gil played for Portugal Davis Cup team against Denmark and won his two matches – the second being a doubles match. By the end of March, Gil was outside the top 100, he started playing qualifying rounds and returned to the Challenger Tour. In May, Gil entered the Estoril Open. After defeating in succession four higher ranked players, including Portuguese number 1 Rui Machado and Guillermo García-López in the semifinals, he became the first Portuguese player to reach the final of an ATP singles event. In the final, Gil lost to defending champion Albert Montañés, after squandering a 3–0 advantage in the final set. At the French Open, he did not make it past qualifying rounds and moved to Challenger. Gil won a singles title in Milan and a doubles title in Lugano before losing in the first round at the Wimbledon Championships to Marcel Granollers. He rebounded with a Challenger doubles title in Turin. Gil played against Cyprus at the Davis Cup in July, winning his two singles and doubles matches. Then, he lost in the early rounds at the Swiss Open and the Connecticut Open, and took part in several Challenger tournaments. At the US Open, Gil lost in the first round to John Isner. However, he partnered Daniel Gimeno-Traver in the doubles event to reach the third round of a Grand Slam tournament for the first time, where they lost