In his early years, Simpson was also a talented golfer, baseballer and soccer player, and was known for being a confident and tenacious competitor. He raised money to buy his first set of golf clubs by collecting lost balls from Marrickville Golf Course and selling them second hand. Even at a young age, Simpson was known as an unrelenting competitor. He appealed loudly against brother Jack for leg before wicket (lbw) in a club match in spite of a loud edge; the umpire did not hear the favour and upheld the appeal. In a match in 1956, Simpson appealed for lbw against John Shaw after he had been hit in the head by a low bouncer from Pat Crawford, whereas his teammates were busy coming to the aid of the injured batsman. Simpson said "I was a naturally ambitious person anyway and never had any doubts I could go further. It sounds cocky but I always believed in my own talents."