Two of those defeats occurred in previous finals at Queen's Club in 2001 and 2002, much to the disappointment of the always partizan British crowd.
He also lost to Hewitt in the 2002 Wimbledon semi-final, as Hewitt went on to secure his one, and so far only title at SW19.
Saturday's match should prove a good form-guide going into the third grand slam of the year, and provide the winner with a chance of taking on the rocket-serving Andy Roddick in the final as he chases a fourth consecutive Queen's title, should he overcome compatriot James Blake is his semi-final.
ATP Queen's Club
Hewitt king of Queen's
18/06/2006 AT 14:29
Hewitt refused to be daunted by his recent defeat to the Oxford-born Henman, insisting that he was looking forward to perhaps getting his own back.
"It's always good fun playing Tim," said Hewitt, "it will be great to test each other out before Wimbledon.
"He's looking pretty confident on grass this year, so it's going to be a tough match."
Typically tongue-in-cheek, Henman seems in good spirits after finally reuniting himself with his favoured surface, and would appear to be backing himself to upset the Australian once again.
"Lleyton is a great grass-court player and has beaten me enough times," he said. "But at least I beat him the last time."
ATP Queen's Club
Hewitt aiming to end drought against Blake
18/06/2006 AT 10:34
ATP Queen's Club
Hewitt into 4th Queen's final
17/06/2006 AT 19:34