League
Cup
2000-2001
| Under 8 | Under 9 | Under 10 | Under 11 | Under 12 |
| Under 13 | Under 14 | Under 15 | Under 16 | Under 18 |
Under 8
First Round
| Bye | V | Oak Athletic | |
| Real 60 Cubs | 19 | Lordswood | 0 |
| Bye | V | Sheerness Steel | |
| Wigmore Youth | V | Bye | |
| Swallows | 0 | Cuxton 91 | 4 |
| Bye | V | Cliffe Woods Colts | |
| Swallows 2000 | 2 | Black Lion | 9 |
| Deanview 95 | V | Bye | |
| Thamesview Youth | 5 | Valley Colts | 6 |
| Bye | V | Fulston Zebras | |
| Rainham Kenilworth | V | Bye | |
| Thamesview Rangers | 7 | Chatham Colts | 1 |
| Bye | V | Rainham 84 | |
| Rainham United | 5 | Pegasus 81 | 1 |
| Bredhurst Juniors | V | Bye | |
| Walderslade | V | Bye |
Second Round
| Oak Athletic | 3 | Real 60 | 15 |
| Sheerness Steel | 1 | Wigmore Youth | 2 |
| Cuxton 91 | 4 | Cliffe Woods Colts | 3 |
| Black Lion | 3 | Deanview 95 | 4 |
| Valley Colts | 4 | Fulston Zebras | 2aet |
| Rainham Kenilworth | 4 | Thamesview Rangers | 2 |
| Rainham 84 | 8 | Rainham United | 0 |
| Bredhurst Juniors | 13 | Walderslade | 0 |
Quarter Final
| Real 60 | 3 | Wigmore Youth | 2 |
| Cuxton 91 | 3 | Deanview 95 | 4 |
| Valley Colts | 3 | Rainham Kenilworth | 2 |
| Rainham 84 | 5 | Bredhurst Juniors | 1 |
Semi- Finals
| Deanview 95 | 1 | Valley Colts | 2 |
| Real 60 | 1 | Rainham 84 | 0 |
Final
| Real 60 | 0 | Valley Colts | 4 |
| Deanview 95 | 1 | Fulson Zebras | 4 |
| Bye | V | Rainham United | |
| Thamesview Youth | 3 | Spartac | 2 |
| Pegasus 81 | V | Bye | |
| Swallows | 7 | Rainham 84 Rascals | 0 |
| Bye | V | Strood 87 | |
| Rainham 84 | 2 | Borstal 88 | 1 |
| Black Lion | V | Bye | |
| Wigmore Youth | 3 | Lordswood | 4aet |
| Bye | V | Chatham Colts | |
| Bredhurst Juniors | 1 | Rainham Kenilworth | 8 |
| Cuxton 91 | V | Bye | |
| Real 60 Tigers | 10 | Woodcoombe Youth | 2 |
| Bye | V | Cliffe Woods Colts | |
| Oak Athletic | 11 | Royal Princes Park | 1 |
| Valley Colts | V | Bye |
Second Round
| Fulston Zebras | 0 | Rainham United | 1 |
| Thamesview Youth | 6 | Pegasus 81 | 3 |
| Swallows | 3 | Strood 87 | 2 |
| Rainham 84 | 8 | Black Lion | 2 |
| Lordswood Juniors | 4 | Chatham Colts | 2 |
| Rainham Kenilworth | 8 | Cuxton 91 | 2 |
| Real 60 Tigers | 2 | Cliffe Woods Colts | 5 |
| Oak Athletic | 4 | Valley Colts | 3 |
Quarter Finals
| Rainham United | 8 | Thamesview Youth | 1 |
| Swallows | 2 | Rainham 84 | 0 |
| Lordswood | 3 | Rainham
Kenilworth (RK win on pens) |
3 |
| Cliffe Woods Colts | 9 | Oak Athletic | 3 |
Semi - Finals
| Rainham Kenilworth | 3 | Cliffe Woods Colts | 4aet |
| Swallows | 3 | Rainham United | 2 |
Final
| Cliffe Woods Colts | 8 | Swallows | 0 |
First Round
| Lordswood | 6 | Malling Rangers | 7 |
| Bredhurst Juniors | 3 | Chatham Colts | 2 |
| Bye | V | Real 60 Cougars | |
| Horsted | 3 | Black Lion | 4 |
| Thamesview Youth | 15 | Scorpions | 0 |
| Valley Colts | V | Bye | |
| Cuxton 91 | 1 | Fulston Zebras | 9 |
| Rainham 84 | 3 | Cliffe Woods Colts | 4 |
| Bye | V | Swallows | |
| Spartac | 1 | Rainham United | 13 |
| Cliffe Royals | 0 | Rainham Kenilworth | 23 |
| Bye | V | Deanview 95 | |
| Oak Athletic | 8 | Borstal
88 |
4 |
| Pegasus 81 | 2 | Wigmore
Youth (Peg 81 win on pens) |
2 |
| Sheerness East Youth | V | Bye | |
| Warden Bay | 0 | Snodland Nomads | 17 |
Second Round
| Malling Rangers | 1 | Bredhurst Juniors | 13 |
| Real 60 | 2 | Black Lion | 4 |
| Thamesview Youth | 2 | Valley
Colts (Thamesview win on pens) |
2aet |
| Fulston Zebras | 1 | Cliffe Woods Colts | 4 |
| Swallows | 14 | Rainham United | 4 |
| Rainham Kenilworth | 7 | Deanview 95 | 0 |
| Oak Athletic | 5 | Pegasus 81 | 1 |
| Sheerness East Youth | 4 | Snodland Nomads | 2 |
Quarter Finals
| Bredhurst Juniors | 10 | Black Lion | 3 |
| Valley Colts | 2 | Cliffe Woods Colts | 5 |
| Swallows | 1 | Rainham
Kenilworth (RK win on pens) |
1aet |
| Oak Athletic | 4 | Sheerness East Youth | 6 |
Semi - Finals
| Bredhurst Juniors | 3 | Cliffe Woods Colts | 5 |
| Sheerness East Youth | 6 | Rainham Kenilworth | 1 |
Final
| Cliffe Woods Colts | 1 | Sheerness East Youth Cliffe Woods win on pens |
1 |
First Round
| Bredhurst Juniors | V | Bye | |
| Omega 92 | 3 | Snodland Nomads | 1 |
| Pegasus 81 Royals | 19 | Spartac | 1 |
| Rainham Kenilworth | 11 | Pegasus 81 Colts | 0 |
| Bye | V | Woodcoombe Youth | |
| Horsted | 5 | Cliffe Woods Colts | 3 |
| Thamesview Youth | 7 | Chatham Colts | 6aet |
| Deanview 95 | 10 | Walderslade | 2 |
| Chatham Riverside | 11 | Real 60 Wildcats | 2 |
| New Ash Green | V | Bye | |
| Scorpions | 1 | Oak Athletic | 9 |
| Swallows | 2 | Rainham United | 3 |
| Strood 87 | 4 | Malling Rangers | 0 |
| Wigmore Youth | 0 | Lordswood | 6 |
| Rainham 84 | 1 | Valley Colts | 2 |
| Cuxton 91 | V | Bye |
Second Round
| Bredhurst Juniors | 2 | Omega 92 | 4 |
| Pegasus 81 Royals | 2 | Rainham Kenilworth | 8 |
| Woodcoombe Youth | 3 | Horsted | 4 |
| Thamesview Youth | 1 | Deanview | 7 |
| Chatham Riverside | 4 | New Ash Green | 2 |
| Oak Athletic | 1 | Rainham United | 5 |
| Strood 87 | 1 | Lordswood Juniors | 3 |
| Valley Colts | 2 | Cuxton 91 | 5 |
Quarter Finals
| Omega 92 | 0 | Rainham Kenilworth | 3 |
| Horsted | 3 | Deanview | 1 |
| Chatham Riverside | 3 | Rainham United | 2 |
| Lordswood | 7 | Cuxton 91 | 1 |
Semi - Finals
| Horsted | 8 | Chatham Riverside | 2 |
| Lordswood Juniors | 4 | Rainham Kenilworth | 2 |
Final
| Horsted | 2 | Lordswood Juniors | 0 |
Preliminary
Round
| New Ash Green | 0 | Spartac | 9 |
| Horsted Bees | 5 | Deanview 95 | 9 |
First Round
| Spartac | 1 | Rainham United | 12 |
| Real 60 Lynx | 1 | Thamesview Youth | 4aet |
| Omega 92 | 2 | Wigmore Wasps | 6 |
| Rainham Kenilworth | 3 | Walderslade | 1 |
| Lordswood | 2 | Sheerness East Youth | 6 |
| Black Lion | 5 | Royal Princes Park | 1 |
| Malling Rangers | 0 | Oak Athletic | 6 |
| Wigmore Youth | 3 | Lansdowne Colts | 0 |
| Cliffe Royals | 3 | Strood 87 | 0 |
| Cliffe Woods Colts | 13 | Rainham 84 | 0 |
| Horsted | 17 | Bleakwood Rangers | 0 |
| Pegasus 81 | 1 | Fulston Zebras | 4 |
| Swallows | 3 | Rainham 84 Rangers | 6 |
| Sheerness Steel Youth | 2 | Chatham Colts | 7 |
| Cuxton 91 | 2 | Woodcoombe Youth | 6 |
| Valley Colts | 3 | Deanview 95 | 6 |
Second Round
| Rainham United | 1 | Thamesview Youth | 4 |
| Wigmore Wasps | 2 | Rainham Kenilworth | 1 |
| Sherness East Youth | 8 | Black Lion | 3 |
| Oak Athletic | 1 | Wigmore Youth | 11 |
| Cliffe Royals | 0 | Cliffe Woods Colts | 10 |
| Horsted | 5 | Fulston Zebras | 1 |
| Rainham 84 Rangers | 1 | Chatham Colts | 0 |
| Woodcoombe Youth | 7 | Deanview 95 | 2 |
Quarter Finals
| Thamesview Youth | 0 | Wigmore
Wasps (WW win on pens) |
0 |
| Sheerness East Youth | 7 | Wigmore Youth | 3 |
| Cliffe Woods Colts | 5 | Horsted | 0 |
| Rainham 84 Rangers | 4 | Woodcoombe Youth | 2 |
Semi - Finals
| Cliffe Woods Colts | 22 | Rainham 84 Rangers | 0 |
| Sheerness East Youth | 3 | Wigmore Wasps | 6 |
Final
| Cliffe Woods Colts | 8 | Wigmore Wasps | 2 |
First Round
| Chatham Riverside Youth | 5 | New Road | 4 |
| Real 60 Sabres | 6 | Fulston Zebras | 3 |
| Omega 92 | 0 | Bredhurst Juniors | 13 |
| Chatham Colts | 4 | Thamesview Youth | 3 |
| Rainham 84 | 2 | Lordswood Juniors | 1aet |
| Borstal 88 | 0 | Twydall | 7 |
| Rainham 84 Rovers | 2 | Spartac | 6 |
| Cliffe Woods Colts | 3 | Thamesview Rangers | 1 |
| Woodcoombe Youth | V | Bye | |
| Chatham Riverside | 6 | Scorpions | 2 |
| Horsted | 0 | Earl Juniors | 2 |
| Cuxton 91 | 13 | Sheerness East Youth | 2 |
| Oak Athletic | 7 | Deanview 95 | 2 |
| Horsted Sharks | 6 | Sittingbourne Strikers | 3 |
| Wigmore Youth | 2 | Sheppey United | 4 |
| Cliffe Royals | V | Valley Colts |
Second Round
|
Chatham Riverside Youth |
6 | Real 60 | 3 |
| Bredhurst | 4 | Chatham Colts | 1 |
| Rainham 84 | 4 | Twydall | 2 |
| Spartac | 0 | Cliffe Woods Colts | 8 |
| Woodcoombe Youth | 2 | Chatham Riverside | 0 |
| Earl Juniors | 6 | Cuxton 91 | 2 |
| Oak Athletic | 2 | Horsted Sharks | 4 |
| Sheppey United | 7 | Valley Colts | 6 |
Quarter Finals
| Chatham Riverside Youth | 1 | Bredhurst Juniors | 12 |
| Rainham 84 | 6 | Cliffe Woods Colts | 1 |
| Woodcoombe Youth | 3 | Earl Juniors | 0 |
| Horsted Sharks | 4 | Sheppey United | 3 |
Semi - Finals
| Bredhurst Juniors | 4 | Rainham 84 | 3aet |
| Woodcoombe Youth | 1 | Horsted Sharks | 0 |
Final
| Bredhurst Juniors | 2 | Woodcoombe Youth | 1aet |
First Round
| Bye | V | Swallows | |
| Thamesview Youth | 10 | Malling Rangers | 0 |
| Deanview 95 | 6 | Sheerness Steel | 2 |
| Snodland Nomads | 0 | Riverview | 5 |
| Wainscott | V | Bye | |
| New Road | 4 | Woodcoombe Youth | 0 |
| Wigmore Youth | 1 | Cliffe Woods Colts | 4 |
| Borstal 88 Lions | 7 | Chatham Colts | 2 |
| Bye | V | Lordswood | |
| Omega 92 | 2 | Cliffe Royals | 3 |
| Rainham 84 | 2 | Wigmore Athletic | 4 |
| Chatham Riverside | 5 | Horsted | 3 |
| Real 60 Pumas | V | Bye | |
| Spartac | 2 | Oak Athletic | 5 |
| Bredhurst Juniors | 17 | Scorpions | 1 |
| Valley Colts | V | Bye |
Second Round
| Swallows | 0 | Thamesview Youth | 8 |
| Deanview 95 | 3 | Riverview United | 1 |
| Wainscott | 2 | New Road | 6 |
| Cliffe Woods Colts | 0 | Borstal 88 Lions | 4 |
| Lordswood | 0 | Cliffe Royals | 2 |
| Wigmore Athletic | 2 | Chatham
Riverside (CR win on pens) |
2aet |
| Real 60 Pumas | 4 | Oak Athletic | 0 |
| Bredhurst Juniors | 10 | Valley Colts | 2 |
Quarter Finals
| Thamesview Youth | 3 | Deanview 95 | 2 |
| New Road | 2 | Borstal 88 | 6 |
| Cliffe Royals | 3 | Chatham Riverside | 2 |
| Real 60 | 3 | Bredhurst Juniors | 2 |
Semi - Finals
| Borstal 88 | 2 | Thamesview Youth | 4 |
| Cliffe Royals | 4 | Real 60 | 0 |
Final
| Cliffe Royals | 0 | Thamesview Youth | 6 |
First Round
| Fulston Zebras | 1 | Wigmore Youth | 6 |
| Valley Colts | V | Bye | |
| Bredhurst Juniors | 5 | Oak Athletic | 1 |
| Scorpions | 10 | Marlow Park | 2 |
| Bye | V | Cliffe Woods Colts | |
| Rainham United | 6 | Royal Prnces Park | 3 |
| Rainham 84 | 1 | Wigmore Dynamos | 3 |
| Black Lion | V | Bye | |
| Walderslade | 1 | Earl Juniors | 3 |
| Borstal 88 Aardwolves | 4 | Twydall | 7 |
| Bye | V | Sheppey United | |
| Pegasus 81 | V | Sittingbourne Strikers | |
| Woodcoombe Youth | 3 | Snodland Nomads | 1 |
| Bye | V | Chatham Colts | |
| New Road | 4 | Swallows | 0 |
| Cobham Colts | V | Bye |
Second Round
| Wigmore Youth | 4 | Valley Colts | 1 |
| Bredhurst Juniors | 2 | Scorpions | 1 |
| Cliffe Woods Colts | 15 | Rainham United | 0 |
| Wigmore Dynamos | 4 | Black Lion | 0 |
| Earl Juniors | 2 | Twydall | 4 |
| Sheppey United | 2 | Pegasus 81 | 3 |
| Woodcoombe Youth | 4 | Chatham Colts | 2 |
| New Road | 0 | Cobham Colts | 8 |
Quarter Finals
| Wigmore Youth | 3 | Bredhurst Juniors | 1 |
| Cliffe Woods Colts | 7 | Wigmore Dynamos | 1 |
| Twydall | 1 | Pegasus 81 | 2 |
| Woodcoombe Youth | 0 | Cobham Colts | 5 |
Semi - Finals
| Pegasus 81 | 1 | Cliffe Woods Colts | 0 |
| Wigmore Youth | 1 | Cobham Colts | 5 |
Final
| Cobham Colts | 1 | Pegasus 81 | 5 |
First Round
| Euroflo | 5 | Ridgeview | 1 |
| Wigmore Warriors | 2 | Fulston Zebras | 3 |
| Spartac | 8 | Swallows | 1 |
| Woodcoombe Youth | V | Bye | |
| Scorpions | 1 | Real 60 Lions | 5 |
| Cliffe Royals | 3 | Valley Colts | 6 |
| Bredhurst Juniors | 6 | Rainham Kenilworth | 1 |
| Pegasus 81 | 5 | Chatham Riverside | 0 |
Quarter Finals
| Euroflo | 3 | Fulston
Zebras (Euroflo win on pens) |
3 |
| Spartac | 4 | Woodcoombe Youth | 2 |
| Real 60 | 4 | Valley
Colts (VC win on pens) |
4 |
| Bredhurst Juniors | 11 | Pegasus 81 | 0 |
Semi - Finals
| Euroflo | 1 | Spartac | 2 |
| Valley Colts | 2 | Bredhurst Juniors | 3 |
Final
| Bredhurst Juniors | 0 | Spartac | 3 |
First Round
| Bye | V | De Sales United | |
| Chatham Riverside | 2 | Chatham Riverside Rangers | 4 |
| Rainham 84 | 11 | Pegasus 81 | 2 |
| Bye | V | Wigmore Youth | |
| Real 60 Panthers | 0 | Lordswood | 6 |
| Twydall Eagles | 1 | New Ash Green | 5 |
| Thamesview Youth | 4 | Royal Princes Park | 3 |
| Lordswood Tigers | V | Bye |
Quarter Finals
| De Sales Utd | 2 | Chatham Riverside Rangers | 15 |
| Rainham 84 | 2 | Wigmore
Youth (R84 win on pens) |
2 |
| Lordswood | 4 | New Ash Green | 0 |
| Thamesview Youth | 3 | Lordswood Tigers | 1aet |
Semi - Finals
| Lordswood | 0 | Chatham Riverside Rangers | 3 |
| Rainham 84 | 1 | Thamesview Youth | 0 |
Final
| Chatham Riverside Rangers | 3 | Rainham 84 | 0 |