2021
| Citizen of the Year | Michael Hudson – Ansell |
| Citizen of the Year – Youth | Tate Fairbanks |
| Citizen of the Year – Senior | Ian Flack |
| Community Group or Event of the Year | Mosman Park Sub Branch RSL |
2020
| Citizen of the Year | Timothy Barr |
| Citizen of the Year – Youth | Anthony Stout |
| Citizen of the Year – Senior | Kevin Poyton |
| Community Group or Event of the Year | Neighbourhood Nights |
2019
| Citizen of the Year | Geoff Davey |
| Citizen of the Year – Youth | Olivia Martin |
| Citizen of the Year – Senior | Peter Dring |
| Community Group or Event of the Year | Mosman Park Tennis Club |
2018
| Citizen of the Year | Gill Vivian |
| Citizen of the Year – Youth | Lachie Jones |
| Citizen of the Year – Senior | Margaret Baldwin OAM |
| Community Group or Event of the Year | ICEA Foundation / Mosman Craft Markets |
2017
| Citizen of the Year | Rhonda Miller |
| Citizen of the Year – Youth | Amy Brades |
| Citizen of the Year – Senior | Brian Millmore |
| Community Group or Event of the Year | Mosman Park Community Group |
2016
| Citizen of the Year – Youth | Amelia Bates |
| Community Group or Event of the Year | Mosman Park Netball Club / STOMP! |
2015
| Citizen of the Year | Gwen Speirs |
| Citizen of the Year – Youth | Georgie Carey |
| Community Group or Event of the Year | Leighton Battery Heritage Site (Royal Australian Artillery Historical Society) |
2014
| Citizen of the Year | Dhana Richardson |
| Citizen of the Year – Youth | Alexandra Beerli |
| Community Group or Event of the Year | Mosman Park Community Men’s Shed |
2013
| Citizen of the Year | Laurel Osbourne |
| Citizen of the Year – Youth | Lockie Cooke |
| Community Group or Event of the Year | Friends of Mosman Park Bushland |
2012
| Citizen of the Year | John Law |
| Citizen of the Year – Youth | Emma Crane |
| Community Group or Event of the Year | St Luke’s Anglican Parish – Mosman Park EcoFair |
2011
| Citizen of the Year | Russell Brown |
| Citizen of the Year – Youth | Hannah Murray |
| Community Group or Event of the Year | Friends of Mosman Park Bushland – Bringing Back the Bush |
2010
| Citizen of the Year | Gregory Upton |
| Citizen of the Year – Youth | Emily O’Keeffe |
| Community Group or Event of the Year | Mosman Park Bowling Club |
2009
| Citizen of the Year | Simon Nield |
| Community Group or Event of the Year | Rotary Club of Mosman Park |
2008
| Citizen of the Year | Harold Hardy |
| Community Group or Event of the Year | Total Theatre Spring Festival |
2007
| Citizen of the Year | Joe Fisher |
| Citizen of the Year – Youth | Imogene Blair |
| Community Group or Event of the Year | Mosman Park Primary School P&C 2006 Centenary Celebrations |
2006
| Citizen of the Year | Helen McCormack-Johnston |
| Citizen of the Year – Youth | Sarah Harris |
| Community Group or Event of the Year | Mosman Park Netball Club |
2005
| Citizen of the Year | Susan Tham |
| Citizen of the Year – Youth | Anna White |
| Community Group or Event of the Year | Mosman Park Youth Advisory Council – Ampfest Clash of the Bands |
2004
| Citizen of the Year | Samantha Doust |
| Citizen of the Year – Youth | Madeleine O’Brien |
| Community Group or Event of the Year | Mosman Park Youth Advisory Council |
2003
| Citizen of the Year | Roma Perry |
| Citizen of the Year – Youth | Mitchell Thomas |
| Community Group or Event of the Year | Mosman Park Junior Football Club |
2002
| Citizen of the Year | Arthur Downing |
| Citizen of the Year – Youth | Marcel Neurauter |
| Community Group or Event of the Year | Rotary Club of Mosman Park – Annual Seniors Concert |
2001
| Citizen of the Year | Lindy Brophy |
| Citizen of the Year – Youth | Alice Micenko |
| Community Group or Event of the Year | Mosman Arts Foundation |
2000
| Citizen of the Year | John Hughes |
| Citizen of the Year – Youth | MIchael Downing |
| Community Group or Event of the Year | Town of Mosman Park – Centenary Celebration |
1999
| Citizen of the Year | Malcolm Crane |
| Citizen of the Year – Youth | Kelly O’Mara |
| Community Group or Event of the Year | Rotary Club of Mosman Park – John Hughes Big Walk |
1998
| Citizen of the Year | Horrace Dimmock |
| Community Group or Event of the Year | Rotary Club of Mosman Park – John Hughes Big Walk |
1997
| Citizen of the Year | Ellie Ladner |
| Citizen of the Year – Youth | Michael Clapsis |
| Community Group or Event of the Year | St Hilda’s Anglican School for Girls – Centenary Celebration |
1996
| Citizen of the Year | Colin Bourne |
| Citizen of the Year – Youth | Jessica Spinner |
| Community Group or Event of the Year | Mosman Park Arts Foundation – MOSFEST |
1987/88
| Citizen of the Year | Margaret Baldwin |
1985/86
| Citizen of the Year | Harry Buckland |