Derek is related to a number of other past and present high-profile AFL footballers from the Kickett family, including Dale Kickett and Lance "Buddy" Franklin, who are both his nephews. His other nephews are Byron Pickett and Jarrod Garlett and a well known cousin of his is Nicky Winmar. Kicket played in the junior ranks at Central District in the South Australian National Football League, including their U19s Premiership in 1981. Beginning his senior career in the West Australian Football League with, he was the leading goalkicker at West Perth in 1984. After falling out with the Falcons early in the 1986 season, Kickett along with veteran Peter Spencer applied for a clearance to Claremont, which at first was denied, but accepted a week later. Whilst Spencer played only two senior games for Claremont and returned for his last season to his original home at East Perth, Derek Kickett fitted in perfectly and was a key member of the Tigers’ record-breaking 1987 team that finished with twenty-one consecutive unbeaten matches and their sixth senior flag. Kickett polled 46 votes in the Sandover Medal in 1987, which was the most of any player that season, but was ineligible to win due a suspension for slapping East Fremantle's Tim Gepp. Kickett would have won the Sandover Medal by sixteen votes, had he been eligible. Kickett returned to Central District in 1988 for one season. In 1989, he was recruited by North Melbourne in the Victorian Football League, where he also played only one season before being delisted.
Career with Essendon
In 1990, Kickett moved to the Essendon Football Club, where he played four seasons, and became a popular cult figure, known for confident playing style, high leap, evasive skills and his long kicking ability. He was a renowned exponent of the torpedo punt. He played every match in 1992 and 1993 up to the preliminary final, before being omitted from the Bombers' winning 1993 AFL Grand Final team by coach Kevin Sheedy. The omission continues to be one of the most controversial decisions of Sheedy's coaching career, but Sheedy still defends the decision, stating that Kickett's form was poor and that his lack of endurance would have been a specific weakness for the team against, Essendon's opponent on the day. Kickett immediately walked out on the club, and did not watch the Grand Final, nor celebrate the victory with his teammates. Kickett and Sheedy did not speak to each again until 2018.
Move to Sydney
After leaving Essendon, Kickett was drafted by the Sydney Swans. He played three seasons at Sydney, and his last game of AFL football was in the 1996 AFL Grand Final, which Sydney lost against North Melbourne. Kickett returned to the WAFL in 1997, and played that season with Subiaco, before retiring. Kickett has made several appearances in the E. J. Whitten Legends Game. In 2007, he ran development programs for AFL Victoria working with indigenous children.
