Whitecross competed in the main singles draw at the Australian Open six times, without ever making it past the opening round. The closest he came was in the 1982 Australian Open when he lost to Damir Keretić in five sets, after claiming the first two. He also appeared at least once at the other three Grand Slam tournaments, playing in the 1980 US Open (beaten by Víctor Pecci), the 1980 Wimbledon Championships (in the men's doubles), the 1982 Wimbledon Championships (lost to Eddie Edwards), the 1984 Wimbledon Championships (in the mixed doubles), and the 1984 French Open (in the men's doubles).