John Leeds Memorial Trophy
1998-1999
| Under 8 | Under 9 | Under 10 | Under 11 | Under 12 |
| Under 13 | Under 14 | Under 15 | Under 16 | Under 18 |
| Deanview 95 | Bye | |||||
| Thamesview Youth | Bye | |||||
| Valley Colts | 1 | Wigmore Youth | 2 | |||
| Rainham Kenilworth | Bye | |||||
| Walderslade | 4 | Borstal 88 | 8 | |||
| Real 60 Cubs | 1 | Chatham Colts | 2 | |||
| Rainham 84 | Bye | |||||
| Lordswood | Bye |
Quarter Finals
| Deanview 95 | 4 | Thamesview Youth | 1 | |||
| Wigmore Youth | 4 | Rainham Kenilworth | 2 | |||
| Borstal 88 | 1 | Chatham Colts | 6 | |||
| Rainham 84 | 6 | Lordswood | 0 |
Semi - Finals
| Rainham 84 | 2 | Deanview 95 | 5 | |||
| Chatham Colts | 2 | Wigmore Youth | 1 |
Final
Venue: Chatham Town FC
| Chatham Colts | 7 | Deanview 95 | 8 |
| Rainham Utd | 3 | Wigmore Youth | 1 | |||
| Cuxton 91 | 8 | Strood 87 | 1 | |||
| Scorpions | 1 | Rainham Kenilworth | 17 | |||
| Lordswood | 2 | Thamesview Youth | 1 | |||
| Pegasus 81 Colts | 0 | Real 60 | 6 | |||
| Omega 92 | 0 | Snodland Nomads | 13 | |||
| Chatham Riverside | 2 | Chatham Colts | 4 | |||
| Bye | Swallows |
Quarter Finals
| Rainham Utd | 4 | Cuxton 91 | 1 | |||
| Rainham Kenilworth | 2 | Lordswood | 0 | |||
| Real 60 | 9 | Snodland Nomads | 4 | |||
| Chatham Colts | 6 | Swallows | 4 |
Semi - Finals
| Real 60 | 2 | Rainham United | 0 | |||
| Chatham Colts | 3 | Rainham Kenilworth | 4 |
Final
Venue: Chatham Town FC
| Rainham Kenilworth | 1 | Real 60 | 3 |
| Deanview 95 | 4 | 1 | Swallows | ||
| Omega 92 | 14 | 0 | Bleakwood Rangers | ||
| Real 60 Lynx | 4 | 3 | Royal Princes Park | ||
| Valley Colts | 3 | 9 | Chatham Colts | ||
| Black Lion | 2 | 1 | Lordswood | ||
| Rainham Kenilworth | 1 | 4 | Wigmore Wasps | ||
| Walderslade | 5 | 3 | Cuxton 91 | ||
| Woodcoombe | 2 | 0 | Cliffe Royals |
First Round
| Deanview 95 | 0 | Omega 92 | 2 aet | |||
| Real 60 | (4) | 4 | Chatham Colts | (4) 2 | ||
| Black Lion | 0 | Wigmore Wasps | 5 | |||
| Walderslade | 0 | Woodcoombe Youth | 3 | |||
| Gravesend Spartans | 6 | Strood 87 | 0 | |||
| New Road | 0 | Fulston Zebras | 5 | |||
| Horsted Bees | 4 | Spartac | 1 | |||
| Old Oak Juniors | 2 | Rainham Utd | 1 |
Quarter Finals
| Omega 92 | 3 | Real 60 | 0 | |||
| Wigmore Wasps | 1 | Woodcoombe Youth | 4 | |||
| Gravesend Spartans | 2 | Fulston Zebras | 3 | |||
| Horsted Bees | 1 | Old Oak Juniors | 2 |
Semi - Finals
Woodcoombe Youth |
3 | Fulston Zebras | 5 | |||
| Old Oak Juniors | 3 | Omega 92 | 6 aet |
Final
Venue: Sittingbourne FC
| Fulston Zebras | 3 | Omega 92 | 2 |
Preliminary Round
| New Ash Green | 0 | 6 | Cuxton 91 | ||||
| Woodcoombe Youth | 3 | 1 | Deanview 95 | ||||
| Omega 92 | 1 | 6 | Lordswood | ||||
| Sheerness East Youth | 8 | 0 | Scorpions | ||||
| Walderslade | V | Chatham Riverside Awarded to CR |
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| Old Oak Juniors | 2 | 7 | Pegasus 81 | ||||
| Fulston Zebras | 2 | 6 | Spartac | ||||
| Real 60 Polecats | 16 | 0 | Borstal 88 | ||||
| Valley Colts | 4 | aet | 3 | Rainham 84 Rovers | |||
| Strood 87 | 2 | 3 | Rainham 84 | ||||
| Chatham Colts | 1 | 2 | Horsted Sharks |
First Round
| Cuxton 91 | 0 |
Woodcoombe Youth | 4 | ||||
| Lordswood | 8 |
Sheerness East Youth | 0 | ||||
| Chatham Riverside | 1 |
Pegasus 81 | 6 | ||||
| Spartac | 0 |
Real 60 | 5 | ||||
| Valley Colts | 1 |
Rainham 84 | 5 | ||||
| Horsted Sharks | 2 |
Wigmore Youth | 0 | ||||
| Cliffe Royals | 3 | Horsted | 1 | ||||
| Rainham Kenilworth | 10 | Earl Juniors | 1 |
| Woodcoombe Youth | 0 | Lordswood | 4 | ||||
| Pegasus 81 | 2 | Real 60 | 7 | ||||
| Rainham 84 | 1 | Horsted Sharks | 2 | ||||
| Cliffe Royals | 1 | Rainham Kenilworth | 2 |
Semi - Finals
| Horsted Sharks | 1 | Lordswood | 0 | |||
| Real 60 | 1 | Rainham Kenilworth | 0 |
Final
Venue: Sittingbourne FC
| Horsted Sharks | 1 | Real 60 | 2 |
Preliminary Round
| Faversham 98 | 5 | 1 | Old Oak Juniors | |||
| Rainham 84 | 2 | 5 | Walderslade | |||
| New Road | 12 | 0 | Scorpions | |||
| Omega 92 | 3 | 1 | Chatham Colts | |||
| Spartac | 2 | 1 | Swallows | |||
| Valley Colts | 10 | 0 | Frindsbury 94 |
First Round
| Faversham 98 | 3 |
Walderslade | 4 |
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| New Road | 7 |
Omega 92 | 1 |
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| Spartac | 4 |
Valley Colts | 3 |
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| Wainscott | 0 | Real 60 Pumas | 3 | ||||
| Borstal 88 Lions | 7 | Chatham Riverside | 2 | ||||
| New Ash Green | 7 | Wigmore Athletic | 2 | ||||
| Euroflo | 10 | Wigmore Youth | 3 | ||||
| Sheerness East Youth | 3 | Snodland Nomads | 5 |
Quarter Finals
| Walderslade | 5 | New Road | 1 | |||
| Spartac | 0 | Real 60 Pumas | 7 | |||
| Borstal 88 Lions | Bye (New Ash Green withdrew) | |||||
| Euroflo | 8 | Snodland Nomads | 1 |
Semi - Finals
| Borstal 88 Lions | 0 | Euroflo Youth | 1 | |||
| Real 60 | 10 | Walderslade | 2 |
Final
At The Garrison Ground
| Euroflo | 0 | Real 60 | 2 |
Preliminary Round
| New Road | 21 | 1 | Marlowe Park | |
| Sittingbourne Strikers | 0 | 5 | Scorpions | |
| Rainham Utd | 3 | 4 | Warden Bay | |
| Twydall | 5 | 3 | Black Lion | |
| Rainham 84 | 4 | aet | 2 | Old Oak Juniors |
| Walderslade | 3 | 7 | Spartac | |
| Borstal 88 Aardwolves | 3 | 9 | Snodland Nomads | |
| Borstal 88 Bullets | 4 | aet | 3 | Rainham 84 Royals |
First Round
| New Road | 1 |
Scorpions | 5 |
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| Warden Bay | 0 |
Twydall Boys | 7 |
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| Rainham 84 | (3) 6 |
Spartac | (3) 3 aet |
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| Snodland Nomads | 2 |
Borstal 88 Bullets | 1 |
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| Woodcoombe Youth | 3 | Valley Colts | 2 | ||||
| Earl Juniors | 5 | New Ash Green | 3 | ||||
| Fulston Zebras | 3 | Wigmore Youth | 4 | ||||
| Royal Princes Park | 0 | Sheerness East Youth | 17 |
Quarter Finals
| Scorpions | 7 | Twydall Boys | 3 | |||
| Rainham 84 | 1 | Snodland Nomads | 10 | |||
| Woodcoombe Youth | 3 | Earl Juniors | 0 | |||
| Wigmore Youth | 0 | Sheerness East Youth | 8 |
Semi - Finals
| Woodcoombe Youth | 3 | Sheerness East Youth | 4 | |||
| Scorpions | 3 | Snodland Nomads | 2 |
Final
At The Garrison Ground
| Sheerness East Youth | (3) 0 | Scorpions | (3) 1 |
Preliminary Round
| Lordswood | 6 | aet | 3 | Euroflo |
First Round
| Lordswood | 4 |
Chatham Riverside | 1 | ||||
| Wainscott | 5 | Ridgeview | 1 | ||||
| Pegasus 81 | 20 | Chatham Colts | 0 | ||||
| Twydall | 3 | Valley Colt Tigers | 7 | ||||
| Wigmore Youth | (4) 1 | Fulston Zebras | (4) 3 | ||||
| Sheerness Steel | 3 | Walderslade | 4 | ||||
| Wigmore Warriors | 3 | Rainham Utd | 5 | ||||
| Woodcoombe Youth | 1 | Omega 92 | 5 |
Quarter Finals
| Lordswood | 3 | Wainscott | 2 | |||
| Pegasus 81 | 4 | Valley Colt Tigers | 5 | |||
| Fulston Zebras | 9 | Walderslade | 2 | |||
| Rainham Utd | 1 | Omega 92 | 2 |
Semi - Finals
| Lordswood | 6 | Omega 92 | 1 | |||
| Fulston Zebras | 1 | Valley Colt Tigers | 2 |
Final
At The Garrison Ground
| Lordswood | 3 | Valley Colt Tigers | 2 |
First Round
| Scorpions | Bye | ||||||
| Fulston Zebras | 7 | Featherby | 1 | ||||
| New Road | 10 | Woodcoombe Youth | 3 | ||||
| New Ash Green | 2 | Omega 92 Rangers | 3 | ||||
| Chatham Riverside | (1) 3 | Rainham 84 Raiders | (1) 3 | ||||
| Chatham Riverside won 4-1 on pens | |||||||
| Sheerness East Youth | 3 | Cliffe Woods Colts | 2 | ||||
| Pegasus 81 | 1 | Rainham Kenilworth Raiders | 2 | ||||
| Earl Juniors | w/o | Ridgeview |
Quarter Finals
Scorpions |
1 | Fulston Zebras | 0 | |||
New Road |
6 | Omega 92 Rangers | 3 | |||
Chatham Riverside |
2 | Sheerness East Youth | 4 | |||
Rainham Kenilworth Raiders |
2 | Earl Juniors | 1 |
Semi - Finals
| Rainham Kenilworth Raiders | 7 | Scorpions | 4 aet | |||
| Sheerness East Youth | 2 | New Road | 0 |
Final
At The Garrison Ground
| Rainham Kenilworth Raiders | 0 | Sheerness East Youth | 2 |
First Round
| Thamesview Youth | 7 | Wigmore Youth | 3 | ||||
| Riverview | 2 | Sheerness Steel | 6 | ||||
| Scorpions | 0 | Cobham Colts | 12 | ||||
| Spartac | 6 | Royal Princes Park | 0 | ||||
| Chatham Riverside Youth | 3 | Lordswood | 7 | ||||
| New Ash Green | 0 | Twydall Hawks | 3 | ||||
| Pegasus 81 | 2 | Chatham Riverside | 4 | ||||
| Hoo Rangers | 5 | Walderslade | 8 |
Quarter Finals
| Thamesview Youth | 6 | Sheerness Steel | 7 | |||
| Cobham Colts | 7 | Spartac | 1 | |||
| Lordswood | 4 | Twydall Hawks | 2 | |||
| Chatham Riverside | 2 | Walderslade | 5 |
Semi - Finals
| Lordswood | 1 | Walderslade | 4 | |||
| Cobham Colts | 5 | Sheerness Steel | 4 |
Final
At The Garrison Ground
| Walderslade | 1 | Cobham Colts | 2 |
First Round
| Cliffe Royals | Bye |
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| Valley Colt Tigers | Bye |
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| Medway Royals | Bye |
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| Swale Magpies | Bye |
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| Borstal 88 | Bye |
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| Rainham 84 | 0 | New Ash Green | 8 | ||||
| Frindsbury | 2 | Twydall | 3 | ||||
| Minster Colts | 1 | Valley Colts | 2 |
Quarter Finals
| Cliffe Royals | (0)2 | Valley Colt Tigers | (0)0 | |||
| Medway Royals | 7 | Swale Magpies | 2 | |||
| Borstal 88 | 3 | New Ash Green | 5 | |||
| Twydall | 13 | Valley Colts | 0 |
Semi - Finals
| Twydall | 5 | New Ash Green | 2 | |||
| Cliffe Royals | 0 | Medway Royals | 1 |
Final
At The Garrison Ground
| Twydall | 2 | Medway Royals | 0 |