2009
Kendrick began the year with a loss in the first round of the 2009 Australian Open to Robin Söderling 7–5, 4–6, 4–6, 5–7. He made it to the second round of the Delray Beach International Tennis Championships, before losing to Evgeny Korolev 6–3, 6–6, 5–7, then losing to David Nalbandian in the second round of the BNP Paribas Open 4–6, 4–6. He beat Söderling in the second round of the Sony Ericsson Open, then lost in the third round to Jo-Wilfried Tsonga 5–7, 4–6.
Kendrick did not make it out of the first rounds of the U.S. Men's Clay Court Championships or the Estoril Open. At the 2009 French Open, he beat Daniel Brands 6–7, 7–5, 7–6, 4–6, 6–3, to advance to the second round for the first time in his career, where he lost 5–7, 0–6, 1–6, to Gilles Simon, who had also defeated him at the Estoril Open.
In the first round at Wimbledon, he was beaten by Andy Murray 5–7, 7–6, 3–6, 4–6.
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