| Trophy | Award | Winner | Group | Play | Character | Year |
| Constance Radford | Best Director | Malcolm Todd | West Bridgford Dramatic Society | Seven Stages of an Affair | | 2014 |
| Constance Radford | Best Director | Malcolm Todd | West Bridgford Dramatic Society | Seven Stages of an Affair | | 2014 |
| Constance Radford | Best Director | Alex Hall | West Bridgford Dramatic Society | Henna Night | . | 2012 |
| Constance Radford | Best Director | Simon Carter | Calverton Theatre Group | Shrine | . | 2011 |
| Constance Radford | Best Director | Max Carter | East Leake Amateur Players | Agamemnon | . | 2010 |
| Constance Radford | Best Director | Carol Mullins | Dronfield Players | The Fox | . | 2008 |
| Constance Radford | Best Director | Geoff Allen | Keyworth Dramatic Society | From Here to the Library | . | 2007 |
| Constance Radford | Best Director | James Clarke | Avesbury Crickets | Grimm News - Scene 1 | . | 2006 |
| Constance Radford | Best Director | Chris Ireson | Manchail Productions | The Man with the Christmas Socks | . | 2005 |
| Constance Radford | Best Director | Paul Wilkinson | Gosforth Youth Theatre | The End of the World | . | 2003 |
| Constance Radford | Best Director | Mark Lebeter | Touchwood Theatre | Dream Jobs | . | 2002 |
| Constance Radford | Best Director | Barbara Bradburn | Eccleshall Theatre Company | Permission to Cry | . | 2001 |
| Constance Radford | Best Director | Ken Mitchell | Edwinstowe Theatre Group | . | . | 2000 |
| Constance Radford | Best Director | Jean Crawford | Dilys Guite Players | Semblance of Madness | . | 1999 |
| Constance Radford | Best Director | Harry Bladon | Blaby Drama Group | Resting Place | . | 1998 |
| Constance Radford | Best Director | Simon Ellis | Prospect Players | The Triplets | . | 1997 |
| Constance Radford | Best Director | Jean Lebeter | Edwinstowe Theatre Group | The Train Kept a Rolling | . | 1996 |
| Constance Radford | Best Director | Chad Barnsley | Blaby Drama Group | Shakers | . | 1995 |
| Constance Radford | Best Director | Chad Barnsley | Blaby Drama Group | Cagebirds | . | 1994 |
| Constance Radford | Best Director | Tris Portas | Brampton Youth Theatre | . | . | 1993 |
| Constance Radford | Best Director | Chad Barnsley | Blaby Drama Group | No Why | . | 1992 |
| Constance Radford | Best Director | Karen Peck | Edwinstowe Theatre Group | Hero | . | 1991 |
| Constance Radford | Best Director | Jill Widdowson | Keyworth Dramatic Society | Sunstroke | . | 1990 |
| Constance Radford | Best Director | Sue Cooper | Denys Edwards Players Sheffield | Pastiche | . | 1989 |
| Constance Radford | Best Director | Andrew Davie | Hasland Players Chesterfield | Streuth | . | 1988 |
| Constance Radford | Best Director | Mavis Hyson | Keyworth Dramatic Society | Rock Bottom | . | 1987 |
| Constance Radford | Best Director | Jean Meikle | Chesterfield Playgoers Society | The Good and Obedient Young Man | . | 1986 |
| Constance Radford | Best Director | Tommy Pollendine | Chesterfield Playgoers Society | The Crimson Coconut | . | 1985 |