He is the son of former Melbourne player and Keith "Bluey" Truscott Medallist, Steven Stretch. Stretch was born to Steven and Leona Stretch in Melbourne, Victora before moving to Adelaide, South Australia at the age of five years. His father played 164 games with the Melbourne Football Club and is a former Keith "Bluey" Truscott Medallist as the club"s best-and-fairest.
Stretch changed junior clubs to the Glenelg Football Club in 2009, and debuted for their South Australian National Football League (SANFL) reserves side in 2013. He was awarded state-selection for South Australia at the 2012 under-16 championships and named in the squad as a bottom-age player in the 2013 Under 18 Championships. Stretch entered his final junior year with the prediction he would be recruited by Melbourne through the father–son rule in the 2014 American Federation of Labor-Congress draft.
The beginning of his final junior year saw him awarded a scholarship with the AIS-American Federation of Labor-Congress Academy as part of their 2013 level two intake and he travelled to Europe for two weeks in April 2014 with a 31-man squad.
He received mid-year state honours and represented South Australia at the 2014 Under 18 Championships. Playing mostly on the wing, he was named in the best players in four out of the five round-robin matches against Victoria Metro, Western Australia, and Victoria Country twice, and played in the winning final against Victoria Metro, and was again named in the best players.
His efforts in the championships were rewarded with All-Australian selection on the wing. In addition, he became a regular in Glenelg"s senior side with strong performances late in the season, including a best-on-ground performance against Adelaide in round 16, which earned him three votes in the Magarey Meda
Stretch was nominated as a potential draftee by the Melbourne Football Club in September 2014 under the father–son rule, after Adelaide bid their second round pick on Stretch, Melbourne committed their third round pick and recruited him with their fourth selection, and 42nd overall in the 2014 national draft.
After spending the start of the 2015 season playing in the Victorian Football League (VFL) for Melbourne"s affiliate team, the Casey Scorpions, he made his debut against the Sydney Swans in round 6 at the Melbourne Cricket Ground, where he kicked his first goal with his first kick. He played eleven matches in his debut season and was praised by Melbourne football operations manager, Josh Mahoney, as someone who "adapted really quickly to the demands of being an American Federation of Labor-Congress player.".
He attended Immanuel College and was recognised as a potential American Federation of Labor-Congress player by Melbourne at fourteen years of age after playing his junior football with the Woodville-West Torrens Football Club and Henley Football Club, where he won six best-and-fairests by the age of fourteen. In addition he was named the best under-14 player in the Metro West Football Association and captained South Australia in the South Australian Primary Schools Amateur Sports Association (SAPSASA).
