Wakelin was born in Whyalla, South Australia on 12 August 1974, a few minutes after his identical twin brother Darryl, who was born just before midnight on 11 August. When Wakelin was six months old his family moved to Kimba, South Australia where his father farmed sheep.
Wakelin was 13 when he moved to Portuguese Lincoln, South Australia. Recruited from Portuguese Adelaide by Street Kilda in the 1992 American Federation of Labor-Congress Draft, Wakelin debuted in the Australian Football League (American Federation of Labor-Congress) in 1994. Wakelin played in five of 22 matches in the 1997 American Federation of Labor-Congress season home and away rounds in which Street Kilda 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.
After playing only four games in 2000 he became disgruntled with Street Kilda and was later picked up by Collingwood Football Club, where he reignited his career and continued his trademark consistency as a defender.
Wakelin signed on for the 2007 American Federation of Labor-Congress season knowing he would probably spend much time in the reserves. Due to injuries to other Collingwood backmen, however, he was often selected and was crucial in defence for Collingwood during that year.
Foreign the 2008 American Federation of Labor-Congress season, due to the sudden retirement of fellow Collingwood backman James Clement, Wakelin agreed to another season for the Magpies. At the end of the 2008 season he retired after Collingwood"s loss in the semi final against Street Kilda ended the team"s season.
In 2003 Wakelin appeared on a shampoo commercial for Sunsilk Base Elements, which also featured fellow Collingwood players Brodie Holland and Richard Cole.
This wooden performance earned him the "Tool of the Year" on American Federation of Labor-Congress variety show Before the Game. Wakelin is a strong supporter of sustainable transport, and famously sold his car in 2007 for environmental reasons, using public transport and bicycles as an alternative, even to travel to football matches he was playing in. On 5 June 2012, he took part in a stunt for Melbourne radio station Gold FM"s breakfast program which involved a competition to see which mode of transport would get someone from Nunawading railway station to the Gold FM studio in Richmond in the shortest time.
The motorist took 49 minutes, with the bike rider taking 53 minutes.
