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Ashley is looking at falling even further drop in the rankings as she has to defend a lot of points from March - June 2008, she reached the quarterfinals of the Pacific Life Open in Indian Wells. She upset Lucie Safarova and eight seed Dinara Safina. She then lost to Agnieska Radwanska in the fouth round in three sets 6-2, 4-6 , 6-4 At the Sony Ericsson Open Key Biscayne,Miami,Florida, she reached the third round, the round of 16th , after taking out the 23rd seed Virginie Razzano impressively 6-4 6-4, but lost to Elena Vesnina 4-6 7-5 4-6. While at the Sony Ericsson Open, a large cyst on one of her ovaries burst and she was sent to the hospital. She made it through the ordeal but had to lose one of her ovaries. At the 2008 French Open, she lost 6-2 6-1 against tournament favorite Serena Williams in the first round. After losing on May 25, 2008 at the French Open, Ashley told reporters she would appear in the August 2008 issue of Playboy, a decision she made while convalescing from ovarian cyst surgery in March 2008. She later appeared as the cover girl of the magazine. Thus becoming the first professional tennis player after Vanessa Menga (Playboy Brazil 2001) to grace the pages of Playboy. Won one round at Ordina in the Neatherland over Francesca Schiavone 6-2 6-4, At the 2008 Wimbledon Championships, she lost 6-4 6-3 against 2006 winner Amelie Mauresmo in the first round.