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Olga Poutchkova, coached by her father Alex Poutchkov was No 1 in the World in the ITF U12 rankings in 1999. Olga won the U12 category in the Eddie Herr in 1999, where she beat Shahar Peer 6-2, 6-2 in the final, and a week later was runner up in the U12 category at the Orange Bowl, where qualifier Tatiana Golovin beat her 6-4, 3-6, 6-4.
Olga made her debut on the U18 circuit August 13, 2000 at the USTA Junior International Grass Court Championships where she was defeated in the first round. Just a week later, at the USTA Junior International Hard Court Championships she secured her first win in a U18 doubles match playing alongside Brazilian Caroline Neves. Alongside American Nicole Pitts she won her first U18 Junior tournament (out of 2 in doubles) in Ecuador, January 2001. She won her only U18 Junior title in singles at the US Junior International Hard Court Championships in 2003, beating Jessi Robinson 6-2, 6-2 in the final.
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