Troicki was seeded for the first time in a Grand Slam tournament in Wimbledon Championships, as 30th seed, beating Brian Dabul in straight sets in the first, and winning a five-setter against Daniel Gimeno-Traver in the second round. He lost to Andy Murray in the third round. He then competed in the German Open in Hamburg, losing to eventual finalist Paul-Henri Mathieu 0–3 ret., in the quarterfinals due to a foot injury he suffered when he fell hard in the start of the match. He then lost to Máximo González in Umag in the first round 4–6, 6–3, 6–7. He lost to Marc Gicquel in the second round of the Legg Mason Tennis Classic, 0–3 ret., due to his recurring foot injury suffered in Hamburg after receiving a bye in the first round. He then lost to Ferrer in the first round of the Rogers Masters 3–6, 0–6, and retired in the first round of the Western & Southern Financial Group Masters against Radek Štěpánek, 7–6, 1–0 ret. He had recorded five straight loses. Troicki competed in the US Open as 30th seed and claimed his first victory since Hamburg, defeating Peter Luczak 6–3, 6–3, 1–6, 2–6, 6–1, in the first round, but lost to Julien Benneteau in the following round. He then competed in the 2009 Davis Cup Play-offs, where he won both his matches against Uzbekistan.