"Role of Honour" for the 1999 /2000 season
| Under 8 | Under 9 | Under 10 | Under 11 | Under 12 |
| Under 13 | Under 14 | Under 15 | Under 16 | Under 18 |
| League Cup Winners: | Real 60 Cubs |
| League Cup Runner Up: | Wigmore Youth |
| John Leeds Memorial Trophy Winners: | Rainham Utd |
| John Leeds Memorial Trophy Runner Up: | Black Lion |
| Under 8 East Division Champions: | Valley Cols |
| Under 8 East Division Runners Up: | Old Oak Juniors |
| Under 8 West Division Champions: | Borstal 88 |
| Under 8 West Division Runners Up: | Real 60 Cubs |
| League Cup Winners: | Fulston Zebras |
| League Cup Runner Up: | Black Lion |
| John Leeds Memorial Trophy Winners: | Rainham 84 |
| John Leeds Memorial Trophy Runner Up: | Chatham Colts |
| Under 9 Division 1 Champions: | Cliffe Woods Colts |
| Under 9 Division 1 Runners Up: | Sheerness East Youth |
| Under 9 Division 2 Champions: | Old Oak Juniors |
| Under 9 Division 2 Runners Up: | Black Lion |
| League Cup Winners: | Horsted |
| League Cup Runner Up: | Cliffe Woods Colts |
| John Leeds Memorial Trophy Winners: | Pegasus 81 Colts |
| John Leeds Memorial Trophy Runner Up: | Real 60 |
| Under 10 Division 1 Champions: | Horsted |
| Under 10 Division 1 Runners Up: | Cliffe Woods Colts |
| Under 10 Division 2 Champions: | Woodcoombe Youth |
| Under 10 Division 2 Runners Up: | Omega 92 |
| League Cup Winners: | Horsted |
| League Cup Runner Up: | Cliffe Woods Colts |
| John Leeds Memorial Trophy Winners: | Rainham 84 |
| John Leeds Memorial Trophy Runner Up: | Omega 92 |
| Under 11 Division 1 Champions: | Horsted |
| Under 11 Division 1 Runners Up: | Cliffe Woods Colts |
| Under 11 Division 2 Champions: | Wigmore Youth |
| Under 11 Division 2 Runners Up: | Wigmore Wasps |
| Under 11 Division 3 Champions: | Lansdowne Colts |
| Under 11 Division 3 Runners Up: | New Road |
| League Cup Winners: | Rainham Kenilworth |
| League Cup Runner Up: | Bredhurst Juniors |
| John Leeds Memorial Trophy Winners: | Chatham Colts |
| John Leeds Memorial Trophy Runner Up: | Rainham 84 |
| Under 12 Division 1 Champions: | Cliffe Woods Angels |
| Under 12 Division 1 Runners Up: | Bredhurst Juniors |
| Under 12 Division 2 Champions: | Thamesview Rangers |
| Under 12 Division 2 Runners Up: | Old Oak Juniors |
| Under 12 Division 3 Champions: | Sittingbourne Strikers |
| Under 12 Division 3 Runners Up: | Walderslade |
| League Cup Winners: | Thamesview Youth |
| League Cup Runner Up: | Real 60 |
| John Leeds Memorial Trophy Winners: | Bredhurst Juniors |
| John Leeds Memorial Trophy Runner Up: | Rainham 84 |
| Under 13 Division 1 Champions: | Thamesview Youth |
| Under 13 Division 1 Runners Up: | Real 60 Pumas |
| Under 13 Division 2 Champions: | Borstal 88 Lions |
| Under 13 Division 2 Runners Up: | Old Oak Juniors |
| League Cup Winners: | Cobham Colts |
| League Cup Runner Up: | Pegasus 81 |
| John Leeds Memorial Trophy Winners: | Sheerness East Youth |
| John Leeds Memorial Trophy Runner Up: | Twydall |
| Under 14 Division 1 Champions: | Cobham Colts |
| Under 14 Division 1 Runners Up: | Pegasus 81 |
| Under 14 Division 2 Champions: | Wigmore Youth |
| Under 14 Division 2 Runners Up: | Woodcoombe Youth |
| Under 14 Division 3 Champions: | Valley Colts |
| Under 14 Division 3 Runners Up: | New Ash Green |
| League Cup Winners: | Spartac |
| League Cup Runner Up: | Sittingbourne Strikers |
| John Leeds Memorial Trophy Winners: | Sheppey United |
| John Leeds Memorial Trophy Runner Up: | Fulston Zebras |
| Under 15 Division 1 Champions: | Sheppey Utd |
| Under 15 Division 1 Runners Up: | Spartac |
| Under 15 Division 2 Champions: | Cliffe Royals |
| Under 15 Division 2 Runners Up: | Omega 92 |
| League Cup Winners: | Swale Magpies |
| League Cup Runner Up: | Featherby |
| John Leeds Memorial Trophy Winners: | Rainham 84 |
| John Leeds Memorial Trophy Runner Up: | Sheerness East Youth |
| Under 16 Division Champions: | Swale Magpies |
| Under 16 Division Runners Up: | Snodland Nomads |
| League Cup Winners: | Twydall |
| League Cup Runner Up: | Spartac |
| John Leeds Memorial Trophy Winners: | Twydall Hawks |
| John Leeds Memorial Trophy Runner Up: | Cliffe Royals |
| Under 18 Division 1 Champions: | Spartac |
| Under 18 Division 1 Runners Up: | Twydall |
| Under 18 Division 2 Champions: | Thamesview Youth |
| Under 18 Division 2 Runners Up: | Twydall Hawks |