| Trophy | Award | Winner | Group | Play | Character | Year |
| Harry Penson | Actor of the Year | Ben Gilbert | Lace Market Theatre | Constellations | Roland | 2023 |
| Harry Penson | Actor of the Year | Malcolm Todd | Lace Market Theatre | Pressure | Gp Captain James Stagg | 2022 |
| Harry Penson | Actor of the Year | Josh Hayes | Bonington Players | Ten Times Table | Eric | 2020 |
| Harry Penson | Actor of the Year | Danny Longbottom | Bonington Players | The Foreigner | Charlie Baker | 2019 |
| Harry Penson | Actor of the Year | Jerome Foley | West Bridgford Dramatic Society | Thirty Nine Steps | Richard Hannay | 2018 |
| Harry Penson | Actor of the Year | Joe Goatley | Market Harborough Drama Society | Pink Mist | Arthur | 2017 |
| Harry Penson | Actor of the Year | Andrew Beighton | Argent Theatre | Quartet | Reggie | 2016 |
| Harry Penson | Actor of the Year | Jason Wrightham | Lace Market Theatre | Damages | Howard | 2015 |
| Harry Penson | Actor of the Year | Malcolm Todd | West Bridgford Dramatic Society | Mindgame | Styler | 2014 |
| Harry Penson | Actor of the Year | Steve Atkin | Bonington Players | Brassed Off | Danny | 2013 |
| Harry Penson | Actor of the Year | Rob Goll | Peoples Theatre Company | Macbeth | Macbeth | 2012 |
| Harry Penson | Actor of the Year | Vic Roberts | Bonington Players | Death Of A Salesman | Willy Loman | 2011 |
| Harry Penson | Actor of the Year | Everard Robinson | Kegworth Players | Groping for Words | George | 2010 |
| Harry Penson | Actor of the Year | Christian King | Bonington Players | Popcorn | Wayne Hudson | 2009 |
| Harry Penson | Actor of the Year | Dave Cochrain | West Bridgford Dramatic Society | Dinner | . | 2008 |
| Harry Penson | Actor of the Year | Tony Tomlinson | Bonington Players | A Midsummer Night's Dream | Bottom | 2007 |
| Harry Penson | Actor of the Year | Steve Atkin & Kevin Grant | Bonington Players | Cinderella | Asphyxia & Euthanasia | 2006 |
| Harry Penson | Actor of the Year | Eddie Januszcyk | Bonington Players | Pack of Lies | Bob Jackson | 2005 |
| Harry Penson | Actor of the Year | Chad Barnsley | Blaby Drama Group | Come Fly with Me | Dave | 2004 |
| Harry Penson | Actor of the Year | Alan Spooner | Keyworth Dramatic Society | A Touch of Danger | Max Telligan | 2003 |
| Harry Penson | Actor of the Year | Vic Roberts | Bonington Players | When We Are Married | Albert Parker | 2002 |
| Harry Penson | Actor of the Year | Andrew Straw | West Bridgford Dramatic Society | The Weekend | Stephen | 2001 |
| Harry Penson | Actor of the Year | Mark Lebeter | Edwinstowe Theatre Group | Funny Money | Henry | 2000 |
| Harry Penson | Actor of the Year | Mark Lebeter | Edwinstowe Theatre Group | Rumours | Leonard Cummings | 1999 |
| Harry Penson | Actor of the Year | Mark Lebeter | Edwinstowe Theatre Group | Out of Order | Richard Willey | 1998 |
| Harry Penson | Actor of the Year | Roger Kay | West Bridgford Dramatic Society | Trap for a Lonely Man | Bolton & Jackson | 1997 |
| Harry Penson | Actor of the Year | Alan Heydock | East Bridgford DG | Dead Ringer | Bolton & Jackson | 1996 |
| Harry Penson | Actor of the Year | Geoff Longbottom | West Bridgford Dramatic Society | A Month of Sundays | . | 1995 |
| Harry Penson | Actor of the Year | Geoff Longbottom | West Bridgford Dramatic Society | Gaslight | Jack | 1994 |
| Harry Penson | Actor of the Year | Ted Heath | Newstagers Drama Group | Galileo | Galileo | 1993 |
| Harry Penson | Actor of the Year | Alan Heydock | East Bridgford DG | Two and Two Make Sex | George | 1992 |
| Harry Penson | Actor of the Year | Bob Flower | Newstagers Drama Group | Fur Coat and No Knickers | Nip | 1991 |
| Harry Penson | Actor of the Year | Chris Powell | Prospect Players | King Lear | King Lear | 1990 |
| Harry Penson | Actor of the Year | Dave Pearce | Penson Players | Death Trap | . | 1989 |
| Harry Penson | Actor of the Year | Steve Bentley | East Bridgford DG | Habeas Corpus | . | 1988 |
| Harry Penson | Actor of the Year | Steve Bentley | East Bridgford DG | . | . | 1987 |
| Harry Penson | Actor of the Year | John Chambers | Keyworth Dramatic Society | Darling Mr London | . | 1986 |
| Harry Penson | Actor of the Year | Harvey Deaton | Wollaton Drama Group | . | . | 1985 |
| Harry Penson | Actor of the Year | Tony Vokes | West Bridgford Dramatic Society | . | . | 1984 |
| Harry Penson | Actor of the Year | Derek Godfrey | Wollaton Drama Group | . | . | 1983 |
| Harry Penson | Actor of the Year | Mike Ridley | Wollaton Drama Group | . | . | 1982 |
| Harry Penson | Actor of the Year | Chuck Bentley | Co-operative Arts Theatre | Streetcar Named Desire | . | 1981 |
| Harry Penson | Actor of the Year | Roy Ainscough | Keyworth Dramatic Society | . | . | 1980 |
| Harry Penson | Actor of the Year | John Uttley | Co-operative Arts Theatre | Hotel Paradiso | . | 1979 |
| Harry Penson | Actor of the Year | Ken Barnard | St John's Church Dramatic society | Wait Until Dark | . | 1978 |
| Harry Penson | Actor of the Year | Granville Horrey | Huthwaite Amateur Players | . | . | 1977 |
| Harry Penson | Actor of the Year | Geoff Longbottom | Friary Players | . | . | 1976 |
| Harry Penson | Actor of the Year | Bobbie Spate | Keyworth Dramatic Society | . | . | 1975 |
| Harry Penson | Actor of the Year | John Dove | Sherwood Amateur DS | . | . | 1975 |
| Harry Penson | Actor of the Year | Tony Tatton | Co-operative Arts Theatre | Harvey | Elwood P. Dowd | 1974 |
| Harry Penson | Actor of the Year | Stephen Martin | Co-operative Arts Theatre | . | . | 1973 |