His opening tournament of 2006 was the Qatar Open, where he lost in the second round to Tommy Haas 2–6, 6–7 and 7–5 in tie-break. In that year's Australian Open he was defeated in the first round by Russian Dmitry Tursunov, 7–5, 3–6, 4–6, 5–7. His early defeat in the Australian Open was followed by success in the Zagreb Open; Henman reached the semi-finals, but was defeated by Stefan Koubek, 3–6, 6–3, 2–6. His success in Zagreb was met by failure at the Rotterdam Open, where he was beaten in the second round by future world no. 1 Novak Djokovic in three sets, 7–5, 3–6, 4–6. At the Dubai Open Henman reached the quarter-finals, but lost the match to the Spanish world no. 2 Rafael Nadal in straight sets; 6–7 (1–7 in tie break), 1–6. Henman was defeated in the second round of Indian Wells by up-and-comer Tomáš Berdych in two sets, 4–6, 4–6. Henman ended an eight-match losing streak against Lleyton Hewitt on 25 March 2006, with a 7–6, 6–3 victory at the Miami Masters tournament, but lost in the third round to unseeded German Simon Greul in three sets; 6–0, 1–6, 5–7. He was defeated in the first round of the Monte-Carlo Masters by Argentinian world no. 8 Gastón Gaudio, 1–6, 3–6. At the Italian Open Henman managed to reach the third round, but lost to Nadal, 2–6, 2–6. His success in the Italian Open was met with a defeat in the second round of the French Open by Dmitry Tursunov in four sets; 3–6, 2–6, 6–4, 4–6. His run at the Queen's Club Championships was far more successful, with Henman losing to Lleyton Hewitt 6–3, 3–6, 6–2 in the semi-finals.