Redden played minor hockey with the teams at Hillmond High School, and the Mid West Red Wings, which were from the rural area. After that, he played one year with the Lloydminster Blazers, before joining the Western Hockey League (WHL)'s Brandon Wheat Kings for the 1993–94 season. In his first year of major junior hockey with Brandon, he was awarded the Jim Piggott Memorial Trophy for WHL rookie of the year honours. The Wheat Kings made it to two Memorial Cup appearances, in 1995 and 1996, whilst Redden was a member of the team. He was also a member of the 1995 and 1996 Canadian teams at the World Junior Hockey Championships, both teams winning gold medals.