Originally Posted by NadalAgassi
Highly doubtful. He has never beaten Hewitt anywhere, not even at Queens on very fast grass when Hewitt was younger. Hewitt is the worst possible matchup for him, with Hewitt or Sampras in the draw he was never winning Wimbledon.
They played twice in 2006 in Miami and Queens. Henman won the first one and was up a set in the latter before he got hosed on a line call and self-destructed.
At his peak, though, Hewitt was a nightmare for Henman because of his passing shots and lob. Best backhand lob in the game still. They played in the SF in 2002 and Hewitt crushed him.
Henman's only other real shot was in 2004 when he lost in the QF to Ancic. Bad tactics there and a real shame since he had beaten Flip in the previous round who was the finalist the year before. Henman beat Roddick earlier that year in Indian Wells and would have had a real shot in the SF. A final with Federer would have been amazing on so many levels.