[3][4] In 1964, Hillebrand and partner Clive Brebnor reached the men's doubles final of the British Hard Court Championships, where they lost to Cliff Drysdale and Keith Diepraam in straight sets.
[5] Hillebrand had wins either in singles or doubles against Frank Sedgman, Neale Fraser, Rex Hartwig, John Newcombe, Tony Roche, Paul McNamee, Peter McNamara, Bob Hewitt, Frew McMillan, and Jaroslav Drobny.
He also has wins over Davis Cup players Mark Cox (GB), Roger Taylor (GB), Keith Diepraam (South Africa), Beppi Merlo (Italy), Pierre Barthes (Fr), Daniel Contet (Fr), Micah Dubitsky (Israel), Andres Licis (Poland), Christian Kuhnke (Germany), Juan Gisbert (Spain), and Nikki Pilic (Yugoslavia).
Singles tournaments he won include Monte Carlo, Chapel Allerton, Sutton Coalfield, Eastbourne, Hoylake, St. Annes-On-Sea, and Israel.
Jensen arranged for him to immediately play a senior tournament in Costa Mesa, where he met Dr. Jim Pugh, a dentist and tennis player.