He has held solo exhibitions at Watters, Canberra Contemporary Art Space (CCAS), Karen Woodbury, Legge Gallery, and at Helen Maxwell Gallery. His most recent exhibition, Notations: The son and heir of nothing in particular: one more time for the record was shown at Nancy Sever Gallery in Canberra.

Other recent solo exhibition include When He’s at Home He’s a Tourist, CCAS (2017), Hundstag, Watters Gallery (2016), Pink, Watters Gallery (2014) Lost in a Kiss Commissioned Installation, (2009 & 2010) Allens Arthur Robinson, Deutsche Bank Building, Sydney While you were art, new prints Helen Maxwell Gallery, Canberra, Paintings Karen Woodbury Gallery and Derek O’Connor: 10 Year selection, Canberra Museum and Gallery (2007).

He has also participated in numerous group exhibitions including the 20 Years of Collecting, CMAG, Canberra (2018), B5761626572 (2015), M16 Gallery, Canberra Velocity, Drill Hall Gallery, Canberra (2014) Blake Prize, National Art School, Sydney (2009), Mosman Art Prize, Mosman Art Gallery, New South Wales (2007); Arthur Guy Memorial Painting Prize, Bendigo Art Gallery (finalist) (2007); Del Kathryn Barton, Cathy Blanchflower, Derek O’Connor and Monika Tichacek, Karen Woodbury Gallery, Melbourne (2004); Scratch the Surface: Recent Portraiture, Canberra Contemporary Art Space (2003); It’s a Beautiful Day: New Painting in Australia 2, Ian Potter Museum of Art, Melbourne and Art Gallery of New South Wales, Sydney (2002-03); The Redlands Westpac Art Prize, Mosman Art Gallery, New South Wales (2003); On the Brink: Abstraction of the 90s, Heide Museum of Modern Art, Melbourne (2000).

Derek has received several grants and awards over the years. Of particular note are the Capo Fellowship Award, Canberra (2007); Canberra Contemporary Art Space Inaugural Art Prize (2003); Individual Artist Grant, Department of Arts and Culture, Canberra (1998); and the Pat Corrigan Award for Exhibition Development (1995).

His work is held in major public galleries, including the National Gallery of Australia, Canberra; the National Gallery of Victoria, Melbourne; Woolongong University and the Canberra Museum and Art Gallery, as well as important private and corporate collections such as ABN AMRO, Allens Arthur Robinson Renzo Piano Building, Sydney; Art and Australia; Artbank; RACV Art Collection; Pan Pacific Collection; and Austcorp.