John Leeds Memorial Trophy
1999/2000 Season
| Under 8 | Under 9 | Under 10 | Under 11 | Under 12 |
| Under 13 | Under 14 | Under 15 | Under 16 | Under 18 |
| Black Lion | 11 | 1 | Walderslade |
| Bredhurst Juniors | 1 | 2 | Rainham Kenilworth |
| Chatham Colts | 0 | 5 | Rainham Utd |
| Deanview 95 | 4 | 3aet | Strood 87 |
| Lordswood | 8 | 1 | Royal Princes Park |
| Thamesview | 3 | 4 | Swallows |
| Valley Colts | 5 | 3 | Cliffe Woods Colts |
Quarter Final
| Black Lion | 7 | 3 | Deanview 95 |
| Lordswood | 2 | 6 | Swallows |
| Rainham Utd | 2 | 1 | Rainham Kenilworth |
| Valley Colts | 12 | 0 | Pegasus 81 |
Semi Final
| Black Lion | 3 | 2 | Valley Colts |
| Rainham Utd | 2 | 2 | Swallows Rainham utd win 1-0 aet |
FINAL (at Chatham Town FC)
| Black Lion | 2 | 4 | Rainham Utd |
| Borstal 88 | 1 | 8 | Wigmore Youth |
| Chatham Colts | 7 | 2 | Real 60 Cougars |
| Deanview 95 | (3) | (3) | Snodland Nomads |
| Pegasus 81 | 0 | 3 | Thameview |
| Rainham 84 | 3 | 0 | Swallows |
| Walderslade | 1 | 5 | Valley Colts |
| Warden Bay | 0 | 7 | Horsted |
Quarter Final
| Deanview 95 | 4 | 6 | Chatham Colts |
| Horsted | 7 | 2 | Rainham Utd |
| Rainham 84 | 8 | 2 | Valley Colts |
| Wigmore Youth | 5 | 3aet | Thamesview Youth |
Semi Final
| Horsted | 0 | 1 | Chatham Colts |
| Wigmore Youth | 1 | 2 | Rainham 84 |
FINAL (at Chatham Town FC)
| Chatham Colts | 1 | 6 | Rainham 84 |
| Chatham Riverside | 9 | 2 | Scorpions |
| Real 60 Wildcats | 5 | 3 | Pegasus 81 |
| Spartac | 2 | 6 | Wigmore Youth |
Second Round
| Chatham Riverside | 1 | 3 | Pegasus 81 Colts |
| Malling Rangers | 1 | 11 | Swallows |
| Omega 92 | (2) 3 | (2) 2 | Cuxton 91 |
| Real 60 Wildcats | 5 | 2 | Bredhurst Juniors |
| Strood 87 | 2 | 5 | Rainham Utd |
| Walderslade | 5 | 2 | Snodland Nomads |
| Wigmore Youth | 1 | 6 | Old Oak Juniors |
| Woodcoombe Youth | 2 | 6 | Valley Colts |
Quarter Final
| Real 60 Wildcats | 4 | 2 | Old Oak Juniors |
| Pegasus 81 Colts | 2 | 1 | Chatham Riverside |
| Walderslade | 5 | 4 | Rainham Utd |
| Swallows | 0 | 2 | Omega 92 |
Semi Final
| Pegasus 81 Colts | 1 | 0 | Omega 92 |
| Walderslade | 1 | 3 | Real 60 Wildcats |
FINAL (at Chatham Town FC)
| Pegasus 81 Colts | 2 | 1 | Real 60 Wildcats |
| Cliffe Royals | 1 | 3 | Rainham 84 |
| Horsted Bees | 2 | 6 | Fulston Zebras |
| Old Oak Juniors | 3 | 0 | Cuxton 91 |
| Omega 92 | 4 | 1 | Lordswood |
| Real 60 Lynx | 5 | 0 | Strood 87 |
| Royal Princes Park | 3 | 5 | Rainham Utd |
| Walderslade | 2 | 1 | Woodcoombe Youth |
| Wigmore Youth | 6 | 0 | Deanview 95 |
| Fulston Zebras | 14 | 3 | Bleakwood Rangers |
| Old Oak Juniors | 13 | 1 | Malling Rangers |
| Omega 92 | 2 | 1 | Black Lion |
| Rainham 84 | 14 | 3 | Valley Colts |
| Rainham Utd | 7 | 1 | Sheerness East Youth |
| Real 60 Lynx | 3 | 0aet | Spartac |
| Walderslade | 2 | 3 | New Road |
| Wigmore Youth | 5 | 0 | Chatham Colts |
Quarter Final
| Wigmore Youth | 6 | 1 | Real 60 Lynx |
| Old Oak Juniors | 3 | 4 | Rainham 84 |
| Rainham Utd | 1 | 2 | Omega 92 |
| Fulston Zebras | 2 | 3 | New Road |
Semi Final
| New Road | 1 | 2 | Rainham 84 |
| Wigmore Youth | 1 | 3 | Omega 92 |
FINAL (at The Garrison Ground)
| Omega 92 | 3 | 3 | Rainham 84 R84 Win on pens |
| Borstal 88 | 1 | 8 | Real 60 Polecats |
| Chatham Riverside | (3)3 | (3)2aet and pens | Cuxton 91 |
| Cliffe Woods Colts | 6 | 1 | Old Oak Juniors |
| Deanview 95 | 1 | 6 | Twydall |
| Fulston Zebras | 0 | 4 | Valley Colts |
| Horsted | 3 | 5 | Scorpions |
| New Ash Green | 1 | 4 | Chatham Riverside Youth |
| Rainham Utd | 0 | 1 | Wigmore Youth |
| Sheerness East Youth | 5 | 4 | Cliffe Royals |
| Sheppey Utd | 0 | 5 | Rainham 84 |
| Strood 87 | 3 | 4 | Thamesview Rangers |
| Walderslade | 0 | 7 | Woodcoombe Youth |
| Chatham Colts | 11 | 0 | Spartac |
| Chatham Riverside | 0 | 3 | Cliffe Woods Colts |
| chatham Riverside Youth | 2 | 4 | Woodcoombe Youth |
| Earl Juniors | 4 | 1 | Omega 92 |
| Real 60 | 7 | 1 | Sheerness East Youth |
| Scorpions | 2 | 8 | Twydall |
| Valley Colts | 0 | 5 | Thamesview Rangers |
| Wigmore Youth | 0 | 2 | Rainham 84 |
Quarter Final
| Real 60 Polecats | 1 | 2 | Twydall |
| Woodcoombe Youth | 2 | 1 | Cliffe Woods Colts |
| Rainham 84 | 3 | 2 | Thamesview Rangers |
| Earl Juniors | 0 | 8 | Chatham Colts |
Semi Final
| Chatham Colts | 3 | 1 | Twydall |
| Rainham 84 | 2 | 1 | Woodcoombe Youth |
FINAL (at The Garrison Ground)
| Chatham Colts | 1 | 0 | Rainham 84 |
| Bredhurst Juniors | 4 | 3 | Walderslade |
| Chatham Riverside | (5)3 | (5)1 | Wigmore Ath |
| Wainscott | 6 | 3 | Horsted |
| Bredhurst Juniors | 13 | 1 | Valley Colts |
| Chatham Riverside | 0 | 9 | Old Oak Juniors |
| New Road | 1 | 2 | Swallows |
| Scorpions | 10 | 1 | Chatham Colts |
| Sheerness East Youth | 2 | 10 | Rainham 84 |
| Spartac | (4) 0 | (4) 2 | Omega 92 |
| Wainscott | 6 | 1 | Snodland Nomads |
| Wigmore Youth | 2 | 3 | Sheerness Steel |
Quarter Final
| Old Oak Juniors | 0 | 6 | Bredhurst Juniors |
| Omega 92 | 0 | 5 | Swallows |
| Rainham 84 | 5 | 3 | Scorpions |
| Wainscott | 3 | 2 | Sheerness Steel |
Semi Final
| Swallows | 1 | 3 | Bredhurst Juniors |
| Wainscott | 2 | 6 | Rainham 84 |
FINAL (at The Garrison Ground)
| Bredhurst Juniors | 3 | 1 | Rainham 84 |
| Black Lion | 4 | 2 | Old Oak Juniors |
| Marlowe Park Youth | 2 | 11 | Cliffe Woods Colts |
| Sheerness East Youth | 7 | 1 | Wigmore Youth |
| Twydall | 6 | 3 | Chatham Colts |
| Black Lion | 2 | 3 | Spartac |
| Cliffe Woods Colts | 7 | 2 | Fulston Zebras |
| Rainham 84 | 0 | 10 | Earl Juniors |
| Rainham Utd | 5 | 1 | Walderslade |
| Royal Princes Park | 2 | 14 | New Ash Green |
| Sheerness East Youth | 3 | 0 | Woodcoombe Youth |
| Sittingbourne Strikers | (3) 1 | (3) 2 | Borstal 88 Aardwolves |
| Twydall | 7 | 0 | Wigmore Dynamos |
Quarter Final
| Cliffe Woods Colts | 6 | 1 | Rainham Utd |
| New Ash Geen | 3 | 2 | Borstal 88 Aardwolves |
| Spartac | 0 | 3 | Sheerness Steel |
| Twydall | 3 | 2 | Earl Juniors |
Semi Final
| Cliffe Woods Colts | 2 | 5 | Twydall |
| Sheerness East Youth | 7 | 1 | New Ash Green |
FINAL (at The Garrison Ground)
| Sheerness East Youth | 2 | 0 | Twydall |
| Chatham Riverside | 5 | 1 | Twydall |
| Omega 92 | 4 | 2 | Cliffe Royals |
| Rainham Utd | 0 | 8 | Sheppey Utd |
| Wainscott | 0 | 5 | Walderslade |
| Wigmore Warriors | 4 | 1 | Ridgeview |
Quarter Final
| Chatham Riverside | (2)4 | (2)0 | Scorpions |
| Omega 92 | 3 | 5 | Woodcoombe Youth |
| Sheppey Utd | 3 | 0 | Walderslade |
| Wigmore Warriors | 1 | 2 | Fulston Zebras |
Semi Final
| Chatham Riverside | 1 | 2 | Sheppey Utd |
| Woodcoombe Youth | 1 | 3 | Fulston Zebras |
FINAL (at The Garrison Ground)
| Fulston Zebras | 0 | 5 | Sheppey Utd |
| Chatham Riverside | 1 | 4 | Fulston Zebras |
Quarter Final
| Fulston Zebras | 1 | 3 | New Ash Green |
| Lordswood | 1 | 3 | Sheernee East Youth |
| Rainham 84 | 6 | 1 | Pegasus 81 |
| Scorpions | Bye |
Semi Final
| New Ash Green | 1 | 2 | Sheerness East Youth |
| Scorpions | 0 | 4 | Rainham 84 |
FINAL (at The Garrison Ground)
| Rainham 84 | 1 | 0 | Sheerness East Youth |
Under 18
First
Round
| Lordswood | 2 | 3 | Chatham Riverside Youth |
| Sheerness Steel | 0 | 4 | Walderslade |
| Twydall Hawks | 6 | 3 | Royal Princes Park |
Quarter Final
| Cliffe Royals | 4 | 2 | Walderslade |
| Real 60 Bobcats | 1 | 7 | Rainham 84 Rangers |
| Twydall Hawks | (3)2 | (3)1 | Chatham Riverside Youth |
| Wigmore Youth | 1 | 5 | Twydall Eagles |
Semi Final
| Cliffe Royals | 5 | 2 | Rainham 84 Rangers |
| Twydall Eagles | 1 | 3 | Twydall Hawks |
FINAL (at Sittingbourne FC)
| Cliffe Royals | 0 | 2 | Twydall Hawks |