Following this, Keothavong began her clay court season by defeating Maret Ani to reach the second round of the Grand Prix in Fes, Morocco where she was defeated by Lourdes Domínguez Lino. This was followed by another first-round defeat in a Premier event in the Italian Open, this one at the hands of Carla Suárez Navarro. In the Madrid Open, she beat Mariana Duque Marino in round one before losing to Lucie Šafářová in the second round. In her very next tournament, she reached the fourth WTA Tour semifinal of her career and her third in 2009 in the Warsaw Open. She faced No. 7 seed, Bethanie Mattek-Sands, in round one, American veteran Jill Craybas in the second round, qualifier Ioana Raluca Olaru in the quarterfinals and was beaten by eighth seed Alona Bondarenko. Nevertheless, in reaching the semifinals she became the first British woman to reach the semifinals of a WTA clay-court event since Jo Durie reached the semifinals of the 1983 French Open, 26 years before. She then came up against reigning world No. 1, Dinara Safina, in the first round of the French Open and endured the dreaded "double bagel" when she was defeated, 0–6, 0–6. Keothavong began her grass court season on home turf with a victory over Sofia Arvidsson in the first round of the Aegon Classic before losing to eventual semifinalist, Sania Mirza, in round two. She was then defeated in the first round of the Aegon International by world No. 28, Sybille Bammer, but saw off a mugger in central London who tried to snatch her handbag before heading to Wimbledon, where she experienced a first round loss to world No. 80, Patricia Mayr.