Catrakilis attended St John's College in Johannesburg where he played for the first team as a 15-year-old and went on to captain the first team in his final school year and played age group rugby for the Lions. He a brief part of the European season following school with the Racing 92 Under 23 side before returning home.
He went on to join False Bay Rugby in Cape Town playing in the Super A League before making the move to UCT to play Varsity Cup. In his first season for the Ikey Tigers he lead them to the Varsity Cup title and was leading points scorer that season.
Joining Western Province a year later he played Currie Cup and Super Rugby with the Stormers before making the move to the Kings who were in Super Rugby at the time before returning to Cape Town. Castrakilis started the first four of Western Province's matches in the 2015 Currie Cup Premier Division and made a further three appearances off the bench – scoring 53 points in his seven appearances – before being released by Western Province to take up a contract with Montpellier.
In January 2015, Catrakilis signed a contract to join French Top 14 side Montpellier and linked up with former South African World Cup winning head coach Jake White.
October 2016 saw him sign a deal with Premiership side Harlequins for the 2017/18 season but after an injury strained 2 years he announced he would be rejoining the Southern Kings ahead of the 2019/21 Pro 14 season
|2013 - present|
|2013 - 2014|
|2013 - 2015|
|2014 - 2015|
|2015 - 2017|
|2017 - 2020|