League Cup
1998-1999
| Under 8 | Under 9 | Under 10 | Under 11 | Under 12 |
| Under 13 | Under 14 | Under 15 | Under 16 | Under 18 |
Under 8
First Round
| Bredhurst Juniors | 3 | Rainham 84 | 1 |
| Borstal 88 | Bye | ||
| Rainham Kenilworth | 3 | Chatham Colts | 6 |
| Walderslade | 0 | Horsted | 20 |
| Lordswood | 6 | Black Lion | 7 * |
| Sheerness East Youth | 5 | Real 60 Cubs | 2 |
* Game awarded to Lordswood (Black Lion illegal swap of players)
Second Round
| Bredhurst Juniors | 6 | Borstal 88 | 1 | |||
| Chatham Colts | 2 | Horsted | 4 | |||
| Lordswood | 0 | Sheerness East Youth | 9 | |||
| Old Oak Juniors | 4 | Valley Colts | 2 | |||
| Snodland Nomads | 4 | Deanview 95 | 2 | |||
| Swallows | 1 | Fulston Zebras | 5 | |||
| Cliffe Woods Colts | 7 | Wigmore Youth | 0 | |||
| Ditton Minors | 5 | Thamesview Youth | 0 |
Quarter Final
| Snodland Nomads | 5 | Horsted | 2 | |||
| Old Oak Juniors | 6 | Bredhurst Juniors | 9 | |||
| Sheerness East Youth | 2 | Ditton Minors | 4 | |||
| Fulston Zebras | 3 | Cliffe Woods Colts | 5 |
Semi- Finals
| Snodland Nomads | 2 | Ditton Minors | 7 | |||
| Bredhurst Juniors | 0 | Cliffe Woods Colts | 4 |
Final
Venue Chatham Town FC
| Ditton Minors |
|
3 | Cliffe Woods Colts | 5 |
First Round
| Snodland Nomads | 1 | Bredhurst Juniors | 2aet | |||
| Strood 87 | 2 | Chatham Riverside | 6 | |||
| Rainham Kenilworth | 11 | Wigmore Youth | 0 | |||
| Real 60 | 0 | Cliffe Woods Colts | 6 | |||
| Horsted | 9 | Thmesview Youth | 0 | |||
| Pegasus 81 Colts | 14 | Scorpions | 1 | |||
| Valley Colts | 3 | Rainham Utd | 1 | |||
| Pegasus 81 | 2 | Walderslade | 3 |
Second Round
| Bredhurst Juniors | (1) 2 | Lordswood | (1)1 | |||
| Chatham Riverside | 2 | Walderslade | 6 | |||
| Rainham Kenilworth | 1 | Cliffe Woods Colts | 11 | |||
| Horsted | 22 | Pegasus 81 Colts | 2 | |||
| Deanview 95 | 10 | Cuxton 91 | 1 | |||
| Valley Colts | 3 | Omega 92 | 2 | |||
| Swallows | 0 | Old Oak Juniors | 3 | |||
| Chatham Colts | 0 | Rainham 84 | 3 |
Quarter Finals
| Bredhurst Juniors | 2 | Deanview 95 | 1 | |||
| Old Oak Juniors | 3 | Rainham 84 | 2 | |||
| Cliffe Woods Colts | 7 | Walderslade | 0 | |||
| Horsted | 11 | Valley Colts | 0 |
Semi - Finals
| Old Oak Juniors | 2 | Bredhurst Juniors | 3 | |||
| Horsted | 1 | Cliffe Woods Colts | 5 |
Final
Venue Chatham Town FC
| Bredhurst Juniors | 0 | Cliffe Woods Colts | 6 |
Preliminary Round
| Bleakwood Rangers | 2 | Horsted Bees | 1 | |||
| Black Lion | 4 | Real 60 Lynx | 3 | |||
| Thamesview Youth | 3 | Gravesend Spartans | 1 |
First Round
| Bleakwood Rangers | 3 | Black Lion | 9 | |||
| Thamesview Youth | 6 | Cuxton 91 | 0 | |||
| Sheerness East Youth | 3 | Wigmore Wasps | 0 | |||
| Valley Colts | 4 | Spartac | 0 | |||
| Walderslade | 0 | Rainham Kenilworth | 2 | |||
| Rainham 84 | 4 | Fulston Zebras | 0 | |||
| Swallows | 1 | Cliffe Woods Colts | 6 | |||
| Chatham Colts | 4 | Lordswood | 2 | |||
| Omega 92 | 4 | Deanview 95 | 5aet | |||
| Woodcoombe Youth | 0 | Old Oak Juniors | 3 | |||
| Cliffe Royals | 5 | Strood 87 | 3 | |||
| Bredhurst Juniors | 7 | Royal Princes Park | 2 | |||
| New Road | 0 | Rainham Utd | 1 |
Second Round
| Black Lion | 0 | Thamesview Youth | 6 | |||
| Sheerness East Youth | 4 | Valley Colts | 0 | |||
| Rainham Kenilworth | 1 | Rainham 84 | 8 | |||
| Cliffe Woods Colts | 11 | Chatham Colts | 1 | |||
| Deanview 95 | 2 | Pegasus 81 | 9 | |||
| Old Oak Juniors | 1 | Horsted | 4 | |||
| Wigmore Youth | 5 | Cliffe Royals | 1 | |||
| Bredhurst Juniors | 5 | Rainham Utd | 2 |
Quarter Finals
| Bredhurst Juniors | 9 | Wigmore Youth | 1 | |||
| Thamesview Youth | (1) 1 | Cliffe Woods Colts | (1) 2 | |||
| Rainham 84 | 6 | Sheerness East Youth | 1 | |||
| Pegasus 81 | 1 | Horsted | 7 |
Semi - Finals
| Rainham 84 | 2 | Bredhurst Juniors | 5 | |||
| Horsted | 5 | Cliffe Woods Colts | 2 |
Final
Venue : Sittingbourne FC
| Bredhurst Juniors | 0 | Horsted | 6 |
Preliminary Round
| Cuxton 91 | 0 | Pegasus 81 | 4 | |||
| Woodcoombe Youth | 11 | Sheerness East Youth | 1 | |||
| Fulston Zebras | 1 | Cliffe Woods Colts | 12 |
First Round
| Pegasus 81 | 3 | Woodcoombe Youth | 0 | |||
| Cliffe Woods Colts | 7 | Valley Colts | 2 | |||
| Bredhurst Juniors | 8 | Wigmore Youth | 0 | |||
| Scorpions | 1 | Omega 92 | 6 | |||
| Chatham Colts | (1)2 | Rainham 84 | (1)3 | |||
| Twydall | 10 | Walderslade | 1 | |||
| Real 60 Polecats | 2 | Horsted Sharks | 3aet | |||
| Chatham Riverside | 1 | Sheppey Utd | 7 | |||
| Thamesview Youth | 5 | Lordswood | 3 | |||
| Old Oak Juniors | 16 | Borstal 88 | 0 | |||
| Earl Juniors | (1)1 | New Ash Green | (1)4 | |||
| Horsted | 3 | Rainham Utd | 6 | |||
| Strood 87 | (2)1 | Cliffe Royals | (2)2 | |||
| Spartac | 1 | Thamesview Rangers | 4 | |||
| Deanview 95 | 2 | Rainham Kenilworth | 3 | |||
| Rainham 84 Rovers | 1 | Cliffe Woods Angels | 15 |
Second Round
| Pegasus 81 | 2 | Cliffe Woods Colts | 3 | |||
| Bredhurst Juniors | 16 | Omega 92 | 1 | |||
| Rainham 84 | 4 | Twydall | 6 | |||
| Horsted Sharks | 3 | Sheppey Utd | 4 | |||
| Thamesview Youth | 9 | Old Oak Juniors | 2 | |||
| New Ash Green | 1 | Rainham Utd | 8 | |||
| Cliffe Royals | 2 | Thamesview Rangers | 6 | |||
| Rainham Kenilworth | 0 | Cliffe Woods Angels | 4 |
Quarter Finals
| Rainham Utd | 0 | Thamesview Rangers | 3 | |||
| Thamesview Youth | (1) 0 | Cliffe Woods Angels | (1) 4 | |||
| Sheppey Utd | 1 | Cliffe Woods Colts | 7 | |||
| Twydall | 1 | Bredhurst Juniors | 3 |
Semi - Finals
| Bredhurst Juniors | 2 | Cliffe Woods Colts | 1 | |||
| Thamesview Rangers | 1 | Cliffe Woods Angels | 4 |
Final
Venue: Sittingbourne FC
| Bredhurst Juniors | 0 | Cliffe Woods Angels | 3 |
First Round
| Old Oak Juniors | 8 | Sheerness East Youth | 1 | |||
| Omega 92 | 1 | Deanview 95 | 4 | |||
| Lordswood | 7 | Wainscott | 1 | |||
| Wigmore Athletic | 3 | Scorpions | 5 | |||
| Chatham Colts | 1 | Snodland Nomads | 3 | |||
| Wigmore Youth | 0 | Thamesview Youth | 8 | |||
| Riverview | 8 | New Ash Green | 0 | |||
| Real 60 Pumas | 10 | Valley Colts | 1 | |||
| Cliffe Woods Colts | 10 | Spartac | 3 | |||
| Faversham 98 | 1 | Euroflo | 4 | |||
| Chatham Riverside | 6 | New Road | 5aet | |||
| Horsted | 5 | Frindsbury 94 | 2 | |||
| Walderslade | 3 | Borstal 88 Lions | 1 | |||
| Rainham 84 | 4 | Swallows | 7 |
Second Round
| Old Oak Juniors | 2 | Deanview 95 | 7 | |||
| Lordswood | 6 | Scorpions | 2 | |||
| Snodland Nomads | 2 | Thamesview Youth | 9 | |||
| Riverview | 3 | Real 60 Pumas | 2 | |||
| Cliffe Woods Colts | 3 | Euroflo | 0 | |||
| Chatham Riverside | 1 | Horsted | 5 | |||
| Walderslade | 4 | Bredhurst Juniors | 8 | |||
| Swallows | 0 | Rainham Kenilworth | 11 |
Quarter Finals
| Deanview 95 | 9 | Horsted | 2 | |||
| Thamesview Youth | 4 | Cliffe Woods Colts | 1 | |||
| Riverview | 2 | Rainham Kenilworth | 1 | |||
| Bredhurst Juniors | 5 | Lordswood | 2 |
Semi - Finals
| Bredhurst Juniors | 0 | Riverview | 4 | |||
| Deanview 95 | 1 | Thamesview Youth | 3 |
Final
At The Garrison Ground
| Riverview | 3 | Thamesview Youth | 4 |
First Round
Royal Princes Park |
1 | Fulston Zebras | 3 | |||
| Cliffe Woods Colts | 18 | Rainham Utd | 0 | |||
| Earl Juniors | 6 | Sittingbourne Strikers | 2 | |||
| New Ash Green | 0 | Lordswood | 9 | |||
| Walderslade | 1 | Real 60 Tigers | 20 | |||
| Black Lion | 5 | Rainham 84 | 0 | |||
| Rainham 84 Royals | 2 | Borstal 88 Bullets | 4 | |||
| Chatham Colts | 7 | Woodcoombe Youth | 3 | |||
| Sodland Nomads | 2 | Pegasus 81 | 3 | |||
| Marlowe Park Youth | 2 | Scorpions | 10 | |||
| Valley Colts | 0 | Rainham Kenilworth | 7 | |||
| New Road | 2 | Spartac | 0 | |||
| Sheerness East Youth | 1 | Bredhurst Juniors | 6 | |||
| Twydall | 11 | Old Oak Juniors | 2 | |||
| Warden Bay | 0 | Chatham Colts | 23 | |||
| Wigmore Youth | 7 | Borstal 88 Aardwolves | 6 |
Second Round
Fulston Zebras |
2 | Cliffe Woods Colts | 5 | |||
| Earl Juniors | 1 | Lordswood | 8 | |||
| Real 60 Tigers | 15 | Black Lion | 1 | |||
| Borstal 88 Bullets | 2 | Chatham Colts | 4 | |||
| Pegasus 81 | 4 | Scorpions | 2 | |||
| Rainham Kenilworth | 7 | New Road | 2 | |||
| Bredhurst Juniors | 4 | Twydall | 2 | |||
| Thamesview Youth | 14 | Wigmore Youth | 0 |
Quarter Finals
| Lordswood | 0 | Thamesview Youth | 1 | |||
| Bredhurst Juniors | 4 | Rainham Kenilworth | 2 | |||
| Real 60 Tigers | 9 | Chatham Colts | 0 | |||
| Cliffe Woods Colts | 0 | Pegasus 81 | 2 |
Semi - Finals
| Bredhurst Juniors | 0 | Thamesview Youth | 8 | |||
| Pegasus 81 | 0 | Real 60 Tigers | 2 |
Final
At The Garrison Ground
| Thamesview Youth | 0 | Real 60 Tigers | 2 |
First Round
| Ridgeview | 2 | Twydall | 6 | |||
| Bredhurst Juniors | 4 | Walderslade | 1 | |||
| Sheerness Steel | 0 | Euroflo | 9 | |||
| Spartac | 8 | Lordswood | 1 | |||
| Pegasus 81 | (3)4 | Woodcoombe Youth | (3)2 | |||
| Black Lion | 14 | Chatham Colts | 2 | |||
| Wigmore Youth | 0 | Valley Colts Tigers | 1 | |||
| Thamesview Youth | 7 | Fulston Zebras | 3 | |||
| Omega 92 | 1 | Sittingbourne Strikers | 2 |
Second Round
| Twydall | 0 | Bredhurst Juniors | 8 | |||
| Euroflo | 2 | Spartac | 3 | |||
| Pegasus 81 | 1 | Black Lion | 7 | |||
| Rainham Utd | 1 | Real 60 Lions | 7 | |||
| Valley Colt Tigers | 5 | Thamesview Youth | 6 | |||
| Sittingbourne Strikers | 5 | Wainscott | 2 | |||
| Sheppey Utd | 5 | Chatham Riverside | 4 | |||
| Scorpions | 10 | Wigmore Warriors | 0 |
Quarter Finals
| Bredhurst Juniors | 0 | Black Lion | 1 | |||
| Thamesview Youth | 3 | Spartac | 5 | |||
| Scorpions | 2 | Sheppey Utd | 1 | |||
| Real 60 Lions | 3 | Sittingbourne Strikers | 5 |
Semi - Finals
| Sittingbourne Strikers | 2 | Spartac | 4 | |||
| Scorpions | (2)0 | Black Lion | (2)3 |
Final
At The Garrison Ground
| Spartac | 3 | Black Lion | 5 |
First Round
| Omega 92 Rangers | 1 | Thamesview Youth | 9 | |||
| New Road | 1 | Cliffe Woods Colts | 2 aet | |||
| Lordswood | 6 | Sheerness East Youth | 0 | |||
| New Ash Green | (4)0 | Rainham Kenilworth Rovers | (4)8 | |||
| Scorpions | 3 | Pegasus 81 | 0 | |||
| Ridgeview | 1 | Rainham 84 | 19 | |||
| Fulston Zebras | 1 | Chatham Riverside | 4 |
Second Round
| Thamesview Youth | 6 | Cliffe Woods Colts | 0 | |||
| Earl Juniors | 0 | Lordswood | 8 | |||
| Rainham Kenilworth Rovers | 10 | Scorpions | 0 | |||
| Rainham 84 | 6 | Chatham Riverside | 2 | |||
| Woodcoombe Youth | 2 | Snodland Nomads | 5 | |||
| Walderslade | 5 | Rainham 84 Raiders | 2 | |||
| Real 60 Panthers | 10 | Featherby | 0 | |||
| Rainham Kenilworth Raiders | 0 | Swale Magpies | 9 |
Quarter Finals
| Walderslade | 0 | Snodland Nomads | 12 | |||
| Thamesview Youth | 4 | Lordswood | 1 | |||
| Real 60 Panthers | 4 | Swale Magpies | 5 | |||
| Rainham 84 | 1 | Rainham Kenilworth Rovers | 6 |
Semi - Finals
| Thamesview Youth | (3) | Rainham Kenilworth Rovers | (3) | |||
| Snodland Nomads | 3 | Swale Magpies | 1 |
Final
At the Garrison Ground
| Snodland Nomads | 1 | Rainham Kenilworth Rovers | 2 |
First Round
| Chatham Riverside | 1 | Cobham Colts | 5 | |||
| Rainham 84 | 7 | Riverview | 0 | |||
| Scorpions | 0 | Twydall Hawks | 2 | |||
| Lordswood | 2 | Chatham Colts | 3 | |||
| Real 60 Bobcats | 4 | Sheerness Steel | 2 | |||
| Walderslade | 5 | Pegasus 81 | 4 | |||
| Fulston Zebras | 6 | Royal Princes Park | 1 | |||
| New Ash Green | 1 | Chatham Riverside Youth | 2 | |||
| Wigmore Youth | 3 | Rainham 84 Rangers | 4 |
Second Round
| Northfleet Eagles | 3 | Cobham Colts | 2 | |||
| Rainham 84 | 4 | Twydall Hawks | 1 | |||
| Chatham Colts | Bye | |||||
| Real 60 Bobcats | (4)4 | Walderslade | (4)2 | |||
| Fulston Zebras | 11 | Chatham Riverside Youth | 1 | |||
| Spartac | 3 | Rainham 84 Rangers | 6 | |||
| Twydall Eagles | 4 | Thamesview Youth | 1 | |||
| New Road | 9 | Hoo Rangers | 1 |
Quarter Finals
| Real 60 Bobcats | 4 | Twydall Eagles | 1 | |||
| Northfleet Eagles | (3)0 | Fulston Zebras | (3)3 | |||
| New Road | 1 | Rainham 84 | 5 | |||
| Chatham Colts | 3 | Rainham 84 Rangers | 2 |
Semi - Finals
| Fulston Zebras | 2 | Chatham Colts | 0 | |||
| Real 60 | 1 | Rainham 84 | 5 |
Final
(At The Garrison Ground)
| Fulston Zebras | 0 | Rainham 84 | 2 |
First Round
| Minster Colts | 3 | De Sales Utd | 5 | |||
| Frindsbury 94 | 9 | Valley Colts | 1 | |||
| Real 60 | 5 | Vallet Colts Tigers | 1 | |||
| Swale Magpies | 3 | Cliffe Royals | 0 |
Second Round
| De Sales Utd | 4 | Frindsbury 94 | 0 | |||
| Real 60 | 2 | Swale Magpies | 1 | |||
| Chatham Riverside | Bye | |||||
| Borstal 88 | 1 | Strood 87 | 3 | |||
| Spartac | 3 | Twydall | 2 | |||
| New Ash Green | 2 | Riverview Utd | 5 | |||
| Medway Royals | 2 | Black Lion | 3 | |||
| Viewpoint Vipers | 5 | Rainham 84 | 3 |
Quarter Finals
| De Sales Utd | 7 | Viewpoint Vipers | 0 | |||
| Spartac | (4) | Strood 87 | (0)* | |||
| Real 60 | 3 | Riverview Utd | 1 | |||
| Black Lion | 9 | Chatham Riverside | 3 |
* Abandoned after 58 Mins - Result stands
Semi - Finals
| Real 60 | 4 | Black Lion | 1 | |||
| Spartac | 3 | De Sales Utd | 1 |
Final
At The Garrison Ground
| Real 60 | 2 | Spartac | 3 |