| Trophy | Series | 2020 winner(s) | 2021 winner(s) |
| Midland Red Saucer | Best Improved Junior Sailor | Not awarded (lockdown) | Gargi Paneesha |
| Topper Champion | Topper Championship | Not previously awarded | Will Cowley |
| Optimist Champion | Optimist Championship | Not previously awarded | Tom Cowley |
| Junior Windsurfing Champion | Windsurfing Junior Championship | Not previously awarded | Tian Zhang |
| Midland Blue Saucer | Most improved Junior Windsurfer | Not previously awarded | Maly Gross |
| Turkish Delight Trophy | Overall commitment & Contribution to Juniors | Not previously awarded | Maly, Jason, Archie |
| Gooden Senior Performer | Veteran’s Champion – Over 70 yrs (Helm/Crew) | Not previously awarded | Arthur Bedford |
| Windsurfing Cup | Overall Windsurfing Champion | Not previously awarded | Sam Birch |
| Special Award | Volunteer of the Year | New Award | Steve Watson |
| Special Award | Most improved Windsurfers | Not previously awarded | Hannah Gunter, Charlie Comerford |
| Ship’s Biscuit | Outstanding Galley Service | Not awarded (lockdown) | Natalia Orgonova |
| Special Award | Outstanding Contribution to the Club | New Award | Phil Reeves |
| Purslow Gun Cup | Summer Wednesday Handicap | Not awarded (lockdown) | Barry Johnson |
| Gooden Juniors Trophy | Junior Race Day Winner | Not awarded (lockdown) | Evan Base |
| Midland Red Plate | Most Improved Adult Sailor | Not awarded (lockdown) | Kate Weaver |
| 3 Dee Cup | Autumn Average Lap | Mark McKeever / KevinHopkins | Chris Martin |
| Frostbite Bowl | Autumn Pursuit Scratch. Late Series | Mark McKeever / Kevin Hopkins | Richard Adams |
| Snowflake Trophy | Autumn Saturday Pursuit Handicap. | Oliver Mason | Paul Young / Jan Kimber |
| Mary Eaves Trophy | Crews Cold Series | Kevin Hopkins | Jan Kimber |
| Meniscus Trophy | Winter Saturday Average Lap Scratch | Mark Mckeever / Kevin Hopkins | No racing (lockdown) |
| Burton Winter Trophy | Winter Saturday Pursuit Scratch | Mark Mckeever / Kevin Hopkins | No racing (lockdown) |
| Ecob Trophy | Winter Saturday Pursuit Handicap | Oliver Mason | No racing (lockdown) |
| Pump Trophy | Spring Average Lap Scratch | No racing (lockdown) | Chris Martin |
| Snipe Cup | Spring Saturday Pursuit Scratch | No racing (lockdown) | Chris Martin |
| Westminster cup | Spring Saturday Pursuit Handicap | No racing (lockdown) | Oliver Mason |
| Waine Cup | Top Female Helm (Warm Series) | No racing (lockdown) | Maria Hilbert |
| Special Award | Top Sailabilty Group | Not previously awarded | Reach For The Stars |
| Special Award | Most improved Sailabilty Sailor | Not previously awarded | Simy Martin |
| Mathews Bowl | Spring Wednesday Pursuit Scratch | No racing (lockdown) | Chris Winters / Freya Mason |
| Hayes Cup | Spring Wednesday pursuit handicap | No racing (lockdown) | Evan Base |
| Scampi Cup | Crews Warm Series Spring/Summer (Saturday) | Nancy Gudgeon | Jan Kimber |
| Summerfield Trophy | Summer Average Lap Scratch | Richard Adams | Mark McKeever / Gracie McKeever |
| Walker Cup | Summer Saturday Pursuit Scratch | Mark Mckeever /Kevin Hopkins | Dean Jung |
| Burton Cup | Summer Saturday Pursuit Handicap | Jim Sawle /Laura Rhodes | Dean Jung |
| Wednesday Shield | Summer Wednesday Scratch | Mark Mckeever / Kevin Hopkins | Richard Adams |
| Patricia Cup | Overall Scratch Pursuit (Saturday) | Mark Mckeever | Paul Young |
| Grimes Cup | Overall Handicap Pursuit (Saturday) | No results | Paul Young |
| Helmsman’s Cup | Merlin Rocket fleet Champions | Matt Smith / Aimee Allsopp | Mark McKeever / Gracie McKeever |
| Challenge Cup | GP14 Fleet Champions | Mark McKeever/ Kevin Hopkins | Chris Winters / Freya Mason |
| Firecracker Trophy | Menagerie Fleet | Richard Adams | Richard Adams |
| Laser Slate | Laser Fleet Champion | Oliver Mason | Dean Jung |
| Mike Poole Barometer | Flag Officer Series (Wednesdays) | No racing (lockdown) | Richard Adams |
| Female Sailor Award | Most successful Sailor (Helm/Crew) | Not previously awarded | Jan Kimber |