1. Caroline Wozniacki. She only reached the number 1 ranking when better players were not actively playing. She manage to win titles from smaller tournaments and gain enough points to be number 1. In fact she has never won a Grand Slam title. The closest she got was a Finalist at the 2009 US Open. She manage to go deep enough in some Grand Slam which helped her to gain points to be number 1. Career 20 titles.
2. Jelena Jankovic. Another former number 1 with similar unimpressive feat as Caroline. Career 13 WTA titles. Manage to be the finalist in the 2008 US Open but never won any Grand Slam. She won enough smaller tournaments that propelled her to number 1 ranking.
3. Dinara Safina. She is no longer actively playing due to injuries. She reached number 1 status by going deep enough in Grand Slams. In fact she was the finalist in the 2008 French Open, 2009 Australian Open and 2009 French Open. This showing along with 12 career WTA titles propelled her to number 1 ranking. Not as lame as Jelena and Caroline but still unimpressive by not winning any Grand Slam.
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