Junior Career
His first major junior coup was when, at aged 14 he claimed the U14 European title. In 2006 he won the Orange Bowl U16 boys singles and was later named the Eddie Herr International 2007 Rising Star.
In 2007, Grigor was the finalist at the Orange Bowl U18 boys singles, losing to Ričardas Berankis of Lithuania. Alongside Vasek Pospisil, he reached the 2007 US Open doubles final, falling to Jonathan Eysseric and Jérôme Inzerillo.
He began the 2008 Grand Slam season with a quarterfinal showing at Roland Garros, losing to Poland's Jerzy Janowicz in three sets. However he went on to win Wimbledon after defeating Henri Kontinen of Finland in the final. He won the title without dropping a set despite playing with a shoulder injury throughout the tournament. The victory saw him join former junior champions Roger Federer and Stefan Edberg and guaranteed him a wildcard entry into the 2009 Wimbledon men's draw. His success continued at the US Open, which he won on September 7, defeating American qualifier Devin Britton in two sets. On his way to the title he also defeated top seed Tsung-hua Yang of Taiwan in the semifinals. After the tournament Dimitrov announced that he was ending his junior career and focusing on improving his ATP ranking. On September 8 he became junior World No. 1 overtaking Tsung-hua Yang. He closed at No. 3 of the junior ranking that year.
Dimitrov compiled a singles win/loss record of 66–25 as a junior (and 42–20 in doubles).
Junior Grand Slam results:
Australian Open: -
French Open: QF (2008)
Wimbledon: W (2008)
US Open: W (2008)
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