Roddick hired Larry Stefanki as his new coach and started working with him on December 1, 2008. Stefanki had previously trained John McEnroe, Marcelo Ríos, Yevgeny Kafelnikov, Fernando González, and Tim Henman. Under Stefanki's guidance, both Rios and Kafelnikov rose to the World No. 1 ranking, and Henman and González reached the top five, including a 2007 Australian Open runner-up finish by Gonzalez.
Roddick began official tournament competition at the Qatar ExxonMobil Open. He defeated Gaël Monfils in the semifinals 7–6, 3–6, 6–3 before losing to Andy Murray in the final. At the Australian Open, Roddick defeated Xavier Malisse in the second round 4–6, 6–2, 7–6(1), 6–2. After victories over Fabrice Santoro and 21st-seeded Tommy Robredo, Roddick played the defending champion and World No. 3 Novak Djokovic in the quarterfinals. Djokovic retired in the fourth set while trailing 6–7(3), 6–4, 6–2, 2–1, which allowed Roddick to reach the fourth Australian Open semifinal of his career. Roddick was defeated there by eventual runner-up Roger Federer 6–2, 7–5, 7–5.
His next tournament was the SAP Open in San Jose, U.S. He snapped a three-match losing streak against Tommy Haas in the quarterfinals 7–5, 6–4 before losing in the semifinals to Radek Štěpánek for the first time in his career 3–6, 7–6(5), 6–4. At the Regions Morgan Keegan Championships in Memphis, U.S., Roddick defeated Australian Lleyton Hewitt in the semifinals 2–6, 7–6, 6–4, to reach the final. He took his first title of the year by beating Štěpánek in the final 7–5, 7–5.
Roddick chose not to defend his Dubai title, with prize money of $2 million, to protest the refusal of the United Arab Emirates to grant Israeli Shahar Pe'er a visa for the Women's Tennis Association event.[15][16] "I really didn't agree with what went on over there", Roddick said.[15][16]
Roddick played both of the spring ATP World Tour Masters 1000 events in the U.S. He was seeded seventh at the BNP Paribas Open in Indian Wells. He defeated defending champion Djokovic in the quarterfinals 6–3, 6–2. His run was ended by World No. 1 Rafael Nadal in the semifinals 6–4, 7–6(4). However, he won the doubles title with partner Mardy Fish. It was his fourth doubles title overall and his second partnering Fish. At the Miami Masters, Roddick beat ninth-seeded Monfils in the fourth round 7–6(2), 6–2 to secure a place in the quarterfinals, where he lost to Federer 6–3, 4–6, 6–4.
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