In 2006, he once again lost his first match at the Medibank International losing to Chris Guccione 6–4, 3–6, 5–7. At the first slam of the year, the Australian Open, he reached the third round again this time to Nicolas Kiefer 3–6, 2–6, 7–5, 2–6. He reached his first semifinal of the year at the ATP Buenos Aires losing to compatriot Carlos Moyá 6–3, 6–7(3–7), 4–6. However. he fell in the first round of the Brasil Open to Flávio Saretta 4–6, 3–6. At the first two Masters event of the year, the Pacific Life Open and NASDAQ–100 Open, losing to Paradorn Srichaphan 2–6, 2–6 in the third round and Dmitry Tursunov 3–6, 6–7(0–7) in the second round, respectively.