In 2008, due to injury from previous year that caused falling in the rankings, she was forced to play mostly at ITF tournaments. She reached four finals, winning three of them, inclung a $75k title at the Open Féminin de Marseille. She started the year as world No. 287, but climbed till the end to No. 104. 2009–10: Breakthrough into the top 100, continues with injuries Flipkens played at the Australian Open, where she recorded her first win there, defeating Rossana de los Ríos, before she was knocked out the tournament by top seed Jelena Janković. On her next appearances, she was eliminated in the first round at U.S. National Indoors, Barcelona Open, Estoril Open and Internationaux de Strasbourg. She then reached another Grand Slam second round at the French Open. She started the grass-court season with a loss at the Rosmalen Championships, but then reached her first Major third round at Wimbledon. She failed to reach her first round of 16, losing to top-seeded Dinara Safina, 5–7, 1–6, after having a set point in the first set. At the US Open, she reached another Grand Slam third round, after straight-sets victories over Jelena Dokic and Anabel Medina Garrigues. She suffered a defeat in the third round, losing to compatriot and eventual champion Kim Clijsters, 0–6, 2–6. In October 2009, she again defeated Medina Garrigues to reach the quarterfinals of the Luxembourg Open, where her compatriot Yanina Wickmayer stopped her from reaching the first semifinal on the WTA Tour. Flipkens reached the top 100 for the first time in her career at the end of 2009. Flipkens continued her good results in 2010. She first reached the quarterfinals at the Hobart International, where she went through qualifying. In the quarterfinal match, she lost to Sara Erani in straight sets. At the Australian Open, Flipkens lost in the first round to another unseeded (her comeback) Justine Henin, 4–6, 3–6. In March, she made her debut at the Premier 5/Premier Mandatory tournaments. On her way to the third round at Indian Wells, she beat Timea Bacsinszky and Aleksandra Wozniack, before she was eliminated by Elena Dementieva. At the French Open, she defeated Ayumi Morita in the first round, 6–1, 6–4, before Maria Sharapova defeated her in straight sets in the second. In the week before Wimbledon, she reached semifinals of the Rosmalen Championships but lost to Andrea Petkovic. At Wimbledon, she lost