The 2009 Pilot Pen Tennis was a tennis tournament played on outdoor hard courts. It was the 41st edition of the Pilot Pen Tennis, and was part of the ATP World Tour 250 Series of the 2009 ATP World Tour, and of the Premier Series of the 2009 WTA Tour. It took place at the Cullman-Heyman Tennis Center in New Haven, Connecticut, United States, from August 21 through August 29, 2009. It was the last event on the 2009 US Open Series before the 2009 US Open.
The following players received wildcards into the singles main draw
The following players received entry from the qualifying draw:
The following player received the lucky loser spot:
The following players received wildcards into the singles main draw
The following players received entry from the qualifying draw:
The following players received the lucky loser spots:
Fernando Verdasco defeated 
Sam Querrey, 6–4, 7–6(8–6)
Caroline Wozniacki defeated 
Elena Vesnina, 6–2, 6–4
Julian Knowle / Jürgen Melzer defeated 
Bruno Soares / 
Kevin Ullyett, 6–4, 7–6(7–3)
Nuria Llagostera Vives / María José Martínez Sánchez defeated 
Iveta Benešová / Lucie Hradecká, 6–2, 7–5.
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