| rowspan="4"| 2003 | Simon Phillips – The Blue Room (Melbourne Theatre Company) | rowspan="2"| Best Direction of a Play | | rowspan="4"| |- | Simon Phillips – Great Expectations| |- | Rachael Griffiths - Proof (Melbourne Theatre Company) | Best Female Actor in a Play | |- | Christopher Gabardi – Cloud Nine (Melbourne Theatre Company) | Helpmann Award for Best Male Actor in a Supporting Role in a Play | |- | rowspan="6"| 2004 | Inheritance | rowspan="2"| Best Play | | rowspan="6"| |- | Frozen | |- | Julian Meyrick – Frozen (Melbourne Theatre Company) | Best Direction of a Play | |- | Helen Morse – Frozen (Melbourne Theatre Company) | Best Female Actor in a Play | |- | Frank Gallacher – Frozen (Melbourne Theatre Company) | Best Male Actor in a Play | |- |Belinda McClory – Frozen (Melbourne Theatre Company) | Best Female Actor in a Supporting Role in a Play | |- | rowspan="5"| 2005 | The Sapphires | Best Play | | rowspan="5"| |- | Pamela Rabe – Dinner (Melbourne Theatre Company) | Best Female Actor in a Play | |- | Richard Piper – The Daylight Atheist (Melbourne Theatre Company) | Best Male Actor in a Play | |- | Urinetown, the Musical (Melbourne Theatre Company) | Helpmann Award for Best Musical | |- | Ros Horin – Through the Wire (Performing Lines in association with Melbourne Theatre Company) | Helpmann Award for Best New Australian Work | |- | rowspan="3"| 2006 | Simon Phillips – King Lear (Melbourne Theatre Company) | Best Direction in a PLay | | rowspan="3"| |- | Hamish Michael – Two Brothers (Melbourne Theatre Company & Sydney Theatre Company) | Best Male Actor in a Supporting Role in a Play | |- | The 25th Annual Putnam County Spelling Bee (Melbourne Theatre Company) | Best Musical | |- | rowspan="3"| 2007 | Jefferson Mays – I Am My Own Wife (Melbourne Theatre Company, Sydney Theatre Company and Hothouse Theatre) | Best Male Actor in a Play | | rowspan="3"| |- | Matthew Newton – The History Boys (Melbourne Theatre Company) | Best Male Actor in a Supporting Role in a Play | |- | Dan Wyllie – The Pillowman (Melbourne Theatre Company) | Best Male Actor in a Supporting Role in a Play | |- | rowspan="3"| 2008 | Genevieve Picot – Rock n Roll