He has an extensive history performing various roles for theatre, and on screen is known for appearing in the comedy drama series Bay of Fires (2023).
[2][3] In 2002 Winspear appeared in Same, same But Different, a major work created by Kate Champion and performed by dance theatre company Force Majeure, along with dancer Roz Hervey, actor Nathan Page, and others.
[5] He was resident director at Sydney Theatre Company for three years (2003–2005), during which time he directed Morph, These People, This Little Piggy, The Metamorphosis, and Thyestes.
[7] He appeared with Marta Dusseldorp in Joanna Murray-Smith's adaptation of Ingmar Bergman's 1973 film Scenes from a Marriage for Queensland Theatre in 2017.
[8] Winspear was an associate artist for the Griffin Theatre Company in Sydney, and has worked as assistant director with Barrie Kosky, Robyn Nevin, Howard Davies, Garry McDonald, and Jean-Pierre Mignon.