Callinan played his junior football in Tasmania, initially at Rokeby, before joining Lauderdale as an Under-16 and Clarence as an Under-18.
Callinan first played senior football for Clarence and was a member of that club's Tasmanian State League premiership winning team in 2000.
[4] In 2007, Callinan moved to Central District in the South Australian National Football League (SANFL).
[4] In four seasons with Central Districts, Callinan won four premierships (2007, 2008, 2009 and 2010), winning the Jack Oatey Medal as best on ground in the 2010 Grand Final, and two club best and fairest awards (2007, 2010).
[10] Before playing football professionally, Callinan earned his living as an Air Conditioning Installer.