The Club Championship Trophies are awarded annually at the Christmas Party to the winners of the Club Championships. There is also a small banner for each winner and one for the winner of the Handicap Trophy. The Handicaps are based on performances by club members at West Midlands orienteering events over the year. The trophies are presented at the club Christmas party in December.
2021
| 2021 OCTAVIAN DROOBERS CLUB CHAMPIONS | ||||
| CATEGORY | AGE CLASS | COURSE | CHAMPION | HANDICAP |
| Boys | M12 and under | Yellow | Max Straube-Roth | Adam Landels |
| Junior Men | M14 & M16 | Light Green | Rupert Powell | N/A |
| Intermediate Men | M18 & M20 | Blue | Luke Cherry | David Knott |
| Open Men | Any Man | Brown | Alastair Landels | Mark Rookledge |
| Senior Men | M40 & M45 | Blue | Mykyta Chubynsky | N/A |
| Veteran Men | M50 & M55 | Blue | Chris McCartney | Tom Jeffries |
| Vintage Men | M60 & M65 | Green | Stan Alexander | Phil Kirk |
| Super Vintage Men | M70 and over | Short Green | Peter Carey | Mike Hampton |
| Girls | W12 and under | Yellow | N/A | N/A |
| Junior Women | W14 & W16 | Light Green | N/A | N/A |
| Intermediate Women | W18 & W20 | Green | N/A | N/A |
| Open Women | Any Woman | Blue | Harriet Lawson | Anne Straube |
| Senior Women | W40 & W45 | Green | N/A | N/A |
| Veteran Women | W50 & W55 | Green | Liz Phillips | Joanne Leigh |
| Vintage Women | W60 & W65 | Short Green | Margaret Willdig | Rachel Alexander |
| Super Vintage Women | W70 and over | Short Green | Sheila Carey | Janet Richardson |
2014
| OD 2014 Champions | Champion | Handicap Winner | ||
| Boys | M12 and under | Yellow | Oliver Lunn | Felix Lunn |
| Junior Men | M14 & M16 | Light Green | Alfie Bullus | Callum Pearman |
| Intermediate Men | M18 & M20 | Blue | Joseph Kwok | Guy Ross |
| Open Men | Any Man | Brown | William Gardner | Matevsz Podsiadly |
| Senior Men | M40 & M45 | Blue | Chris McCartney | Rob Smart |
| Veteran Men | M50 & M55 | Blue | David Lawson | Kevin Ross |
| Vintage Men | M60 & M65 | Green | Richard Gardner | Keith Willdig |
| Super Vintage Men | M70 and over | Short Green | Peter Carey | Trevor Simpson |
| Girls | W12 and under | Yellow | Pippa Smart | Tabitha Lunn |
| Junior Women | W14 & W16 | Light Green | - | - |
| Intermediate Women | W18 & W20 | Green | - | - |
| Open Women | Any Woman | Blue | Harriett Lawson | - |
| Senior Women | W40 & W45 | Green | Lesley Ross | Jo Congo |
| Veteran Women | W50 & W55 | Green | Liz Phillips | Jane Stew |
| Vintage Women | W60 & W65 | Short Green | Sheila Carey | Margaret Willdig |
| Super Vintage Women | W70 and over | Short Green | Hilary Simpson | Sue Bicknell |
2013
| Age Class | Course | Champion | Handicap Winner | |
| Boys | M12 and under | Yellow | Oliver Lunn | Felix Lunn |
| Junior Men | M14 & M16 | Light Green | Stephen Elkington | Alfie Bullus |
| Intermediate Men | M18 & M20 | Blue | Daniel Kotecky | - |
| Open Men | Any Man | Brown (Blue in 2013) | Harrison McCartney | Ondrej Bajgar |
| Senior Men | M40 & M45 | Blue | Chris McCartney | Stuart Heaton |
| Veteran Men | M50 & M55 | Blue | Andy Emmerson | Mike Snell |
| Vintage Men | M60 & M65 | Green | Dave Marr | John Middler |
| Super Vintage Men | M70 and over | Light Green | Roger Hailey | John Wright |
| Age Class | Course | Champion | Handicap Winner | |
| Girls | W12 and under | Yellow | Pippa Smart | Emily Moore |
| Junior Women | W14 & W16 | Light Green | Aimee Morse | Ella-Rose McCartney |
| Intermediate Women | W18 & W20 | Green | - | - |
| Open Women | Any Woman | Blue | Amy Sarkies | - |
| Senior Women | W40 & W45 | Green | Lesley Ross | Suzanne Humphries |
| Veteran Women | W50 & W55 | Green | Melanie Elkington | Jane Stew |
| Vintage Women | W60 & W65 | Light Green | Sheila Carey | Sue Bicknell |
| Super Vintage Women | W70 and over | Light Green | - | - |
2012
| Age Class | Course | Champion | Handicap Winner | |
| Boys | M12 and under | Yellow | Alfie Bullus | Marco Lewis |
| Junior Men | M14 & M16 | Light Green | Stephen Elkington | William Heaton |
| Intermediate Men | M18 & M20 | Blue | Daniel Kotecky | Oliver King |
| Open Men | Any Man | Brown | Thomas Honniball | Keith Willdig |
| Senior Men | M40 & M45 | Blue | Tom Jeffries | Anthony Walker |
| Veteran Men | M50 & M55 | Blue | Andy Emmerson | Andy Heath |
| Vintage Men | M60 & M65 | Green | Mike Hampton | Dave Marr |
| Super Vintage Men | M70 and over | Light Green | Trevor Simpson | Frank Smith |
| Age Class | Course | Champion | Handicap Winner | |
| Girls | W12 and under | Yellow | Emily Moore | - |
| Junior Women | W14 & W16 | Light Green | Rachel Emmerson | Elizabeth Davies |
| Intermediate Women | W18 & W20 | Green | - | - |
| Open Women | Any Woman | Blue | - | - |
| Senior Women | W40 & W45 | Green | Lesley Ross | Suzanne Humphries |
| Veteran Women | W50 & W55 | Green | Margaret Willdig | Frances King |
| Vintage Women | W60 & W65 | Light Green | Sheila Carey | Sue Hallett |
| Super Vintage Women | W70 and over | Light Green | Hilary Simpson | - |
2011
| Age Class | Course | Champion | Handicap Winner | |
| Boys | M12 and under | Yellow | Alfie Bullus | Oliver Smith |
| Junior Men | M14 & M16 | Light Green | Matt Elkington | Stephen Elkington |
| Intermediate Men | M18 & M20 | Blue | Ryan Wilson | - |
| Open Men | Any Man | Brown | Will Gardner | Tom Jeffries |
| Senior Men | M40 & M45 | Blue | Chris McCartney | Bill Nicolson |
| Veteran Men | M50 & M55 | Blue | Barry Elkington | John Middler |
| Vintage Men | M60 & M65 | Green | Bob Brandon | Chris Dwyer |
| Super Vintage Men | M70 and over | Light Green | John Wright | Kim |
| Age Class | Course | Champion | Handicap Winner | |
| Girls | W12 and under | Yellow | Emily Moore | - |
| Junior Women | W14 & W16 | Light Green | Rachel Emmerson | - |
| Intermediate Women | W18 & W20 | Green | Emma Kettley | - |
| Open Women | Any Woman | Blue | Julie Emmerson | Stephanie Ellis-Gray |
| Senior Women | W40 & W45 | Green | Liz Phillips | - |
| Veteran Women | W50 & W55 | Green | Jane Hastings | Margaret Willdig |
| Vintage Women | W60 & W65 | Light Green | Sheila Carey | Sue Bicknell |
| Super Vintage Women | W70 and over | Light Green | Hilary Simpson | - |
| Alfie Bullus | Marco Lewis |
| Stephen Elkington | William Heaton |
| Daniel Kotecky | Oliver King |
| Thomas Honniball | Keith Willdig |
| Tom Jeffries | Anthony Walker |
| Andy Emmerson | Andy Heath |
| Mike Hampton | Dave Marr |
| Trevor Simpson | Frank Smith |
| Emily Moore | - |
| Rachel Emmerson | Elizabeth Davies |
| - | - |
| - | - |
| Lesley Ross | Suzanne Humphries |
| Margaret Willdig | Frances King |
| Sheila Carey | Sue Hallett |
| Hilary Simpson | - |