In 1999, Sawyer won the bronze medal on the novice level at the Canada Winter Games, skating with a bad cold. The following year, he won the national novice title. He skated on the Junior Grand Prix the following season and won the bronze medal at his first event. His fifth-place finish at his second event prevented him from qualifying for the JGP Final. At Nationals, he placed 4th in the junior level. On the JGP the following season, he qualified for the Junior Grand Prix Final, where he placed fifth, and then won the national Junior title. This earned him a trip to the 2002 Junior Worlds, where he placed 11th after performing an entirely new long program.