Knight has been a finalist seven times in the Archibald Prize from 2005, 2006, 2007, 2009, 2010, 2013 and 2019 with portraits were of Richard Gill, Bob Carr, his grandfather Sir Harold Knight, Bill Wright AM, Jason Phu and Adam Cullen respectively, aside from himself. He has been a finalist in the 2005, 2006, 2011 and 2012 Wynne Prize for landscape painting, and the 2013 and 2015 Sir John Sulman Prize. He won the Mosman Art Prize in 2008. In 2012 Knight was a finalist for the first time in the Doug Moran National Portrait Prize with a portrait of Australian painter Jeffrey Smart and in 2014 with a portrait of David Griggs. He has been an Archibald Prize subject twice in 2009 and 2013. A portrait of him by Sarah Hendy was a finalist in the 2013 Archibald Prize. Jasper Knight is the Co-Director of Chalk Horse gallery in Darlinghurst.