Career
Adelaide
Wakelin was selected by Adelaide with the 11th pick in the 1993 Pre-Season draft. After 2 seasons on their list he didn"t play a senior game and was delisted at the end of 1994. Street Kilda
He played his first game in Round 1 of the 1995 season.
His career started superbly with the Saints, averaging 10 disposals in his first season.
Wakelin played in 17 of 22 matches in the 1997 American Federation of Labor-Congress Premiership Season home and away rounds in which Street Kilda Football Club qualified in first position for the 1997 American Federation of Labor-Congress Finals Series, winning the club’s 2nd Minor Premiership and 1st McClelland Trophy. By the end of the 2000 season, the Saints were looking for younger players and Wakelin was traded to Portuguese Adelaide for the fourth selection in the 2000 National Draft (which was then on-traded to Carlton as part of a deal for Aaron Hamill).
In total, he played 115 games for Street Kilda, kicking just 8 goals. Portuguese Adelaide
During 2005 the Wakelin Brothers became the most capped pair of twin brothers overtaking Steven Febey and Matthew Febey.
In Round 12 of 2006, he picked up a career high 22 disposals against West Coast.
In round 5, 2007, Darryl played his 250th game. On 29 August 2007 he announced his retirement from American Federation of Labor-Congress at the season end, which in fact concluded for him as part of the 2007 Portuguese Grand Final team Wakelin has a pharmacy degree from the Victorian College of Pharmacy and runs a pharmacy in Alberton South Australia.