He debuted at state representative level for New South Wales in the 2010 youth eight which contested the Noel Wilkinson Trophy at the Interstate Regatta within the 2010 Australian Rowing Championships.
[4] At the 2017 Australian Championships he won the open men's quad scull national title rowing with Luke Letcher, Caleb Antill and David Watts.
[6] After moving to the UTS Haberfield Rowing Club in 2017 Playfair came into senior Australian representative contention as a sweep oared rower.
[6] Playfair did make the Australian squad for the 2018 international representative season (selected in the Men's Quadruple Scull) however due to illness he had to withdraw from the team.
[6] With Cameron Girdlestone and Campbell and David Watts, Playfair was selected to race Australia's quad scull at the 2019 World Rowing Championships in Linz, Austria.
Hamish is the nephew of Judy Playfair an Australian breaststroke swimmer, who won a silver medal in the 4×100-metre medley relay at the 1968 Mexico Olympics.