This sparked an interest that culminated in him, at the age of 15, being the top junior tennis player in the world and Youth Olympics gold medalist in 1996.

In 2004, Flanagan staged a shock upset when he beat Mark Philippoussis 7–6, 7–6, in the opening round of the Stella Artois Championship at Queen's Club.

35, Victor Hănescu, in the second round of the tournament, before succumbing to Sébastien Grosjean in the last 16, Flanagan was denied a wildcard into Wimbledon.

[2] The victory raised his profile, and put him on a tennis players' special Weakest Link.

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