| First Round | ||||
| 17/01/1959 | Whitstable Town | 0 - 0 | Tunbridge Wells United | |
| 17/01/1959 | Snowdown CW | 2 - 1 | Canterbury City | |
| 17/01/1959 | Faversham Town | 5 - 1 | Erith & Belvedere | |
| 17/01/1959 | Chatham Town | 2 - 2 | Bromley | |
| 17/01/1959 | Bexleyheath & Welling | 0 - 1 | Ashford Town | |
| 17/01/1959 | Betteshanger CW | 2 - 2 | Herne Bay | |
| 21/01/1959 | Tunbridge Wells United | 4 - 2 | Whitstable Town | Replay |
| 21/01/1959 | Bromley | 4 - 1 | Chatham Town | Replay |
| 24/01/1959 | Cray Wanderers | 1 - 1 | Maidstone United | |
| 27/01/1959 | Maidstone United | 2 - 1 | Cray Wanderers | Replay |
| 31/01/1959 | Deal Town | 3 - 2 | Sheppey United | |
| Second Round | ||||
| 31/01/1959 | Ashford Town | 5 - 0 | Ramsgate Athletic | |
| 31/01/1959 | Dartford | 4 - 2 | Herne Bay | |
| 31/01/1959 | Faversham Town | 1 - 3 | Dover | |
| 31/01/1959 | Maidstone United | 3 - 6 | Tonbridge | |
| 31/01/1959 | Sittingbourne | 0 - 2 | Margate | |
| 31/01/1959 | Snowdown CW | 3 - 2 | Tunbridge Wells United | |
| 31/01/1959 | Bromley | 0 - 0 | Gravesend & Northfleet | |
| 04/02/1959 | Gravesend & Northfleet | 7 - 2 | Bromley | Replay |
| 07/02/1959 | Folkestone Town | 2 - 0 | Deal Town | |
| Quarter-Final | ||||
| 14/02/1959 | Tonbridge | 4 - 3 | Gravesend & Northfleet | |
| 14/02/1959 | Snowdown CW | 3 - 1 | Folkestone Town | |
| 14/02/1959 | Margate | 1 - 2 | Dover | |
| 14/02/1959 | Ashford Town | 2 - 0 | Dartford | |
| Semi-Final | ||||
| 07/03/1959 | Tonbridge | 2 - 2 | Snowdown CW | |
| 07/03/1959 | Ashford Town | 1 - 0 | Dover | |
| 11/03/1959 | Snowdown CW | 1 - 4 | Tonbridge | Replay |
| Final | ||||
| 30/03/1959 | Ashford Town | 2 - 1 | Tonbridge | |
| First Round | ||||
| 24/09/1958 | Sittingbourne | 2 - 1 | Folkestone Town | |
| 24/09/1958 | Dartford | p - p | Margate | |
| 24/09/1958 | Tonbridge | p - p | Ramsgate Athletic | |
| 15/11/1958 | Tonbridge | 4 - 1 | Ramsgate Athletic | |
| 17/01/1959 | Dartford | 5 - 3 | Margate | |
| 21/03/1959 | Bexleyheath & Welling | 4 - 0 | Dover | |
| Semi-Final | ||||
| 30/03/1959 | Dartford | 1 - 2 | Sittingbourne | |
| 18/04/1959 | Bexleyheath & Welling | 1 - 3 | Tonbridge | |
| Final | ||||
| 09/05/1959 | Tonbridge | 3 - 2 | Sittingbourne | |
| Preliminary Round | ||||
| 27/08/1958 | Dover | 5 - 0 | Chatham Town | |
| 28/08/1958 | Faversham Town | 1 - 1 | Gillingham Reserves | |
| 17/09/1958 | Gillingham Reserves | 3 - 1 | Faversham Town | Replay |
| First Round | ||||
| 27/08/1958 | Whitstable Town | 1 - 5 | Snowdown CW | 1st Leg |
| 27/08/1958 | Tunbridge Wells United | 1 - 3 | Folkestone Town | 1st Leg |
| 27/08/1958 | Sittingbourne | 4 - 1 | Bexleyheath & Welling | 1st Leg |
| 27/08/1958 | Ashford Town | 6 - 0 | Sheppey United | 1st Leg |
| 28/08/1958 | Deal Town | 3 - 1 | Betteshanger CW | 1st Leg |
| 03/09/1958 | Dover | 3 - 1 | Herne Bay | 1st Leg |
| 03/09/1958 | Folkestone Town | 2 - 2 | Tunbridge Wells United | 2nd Leg |
| 03/09/1958 | Snowdown CW | 10 - 0 | Whitstable Town | 2nd Leg |
| 04/09/1958 | Margate | 2 - 1 | Ramsgate Athletic | 1st Leg |
| 10/09/1958 | Bexleyheath & Welling | 2 - 2 | Sittingbourne | 2nd Leg |
| 10/09/1958 | Sheppey United | 3 - 2 | Ashford Town | 2nd Leg |
| 11/09/1958 | Betteshanger CW | 2 - 2 | Deal Town | 2nd Leg |
| 11/09/1958 | Ramsgate Athletic | 0 - 1 | Margate | 2nd Leg |
| 25/09/1958 | Canterbury City | 2 - 1 | Gillingham Reserves | 1st Leg |
| 02/10/1958 | Herne Bay | 3 - 4 | Dover | 2nd Leg |
| 25/10/1958 | Gillingham Reserves | 1 - 5 | Canterbury City | 2nd Leg |
| Second Round | ||||
| 22/11/1958 | Ashford Town | 0 - 0 | Margate | |
| 11/12/1958 | Canterbury City | 3 - 1 | Deal Town | |
| 10/01/1959 | Dover | 3 - 3 | Snowdown CW | |
| 22/01/1959 | Margate | 3 - 1 | Ashford Town | Replay |
| 24/01/1959 | Folkestone Town | 1 - 1 | Sittingbourne | |
| 07/02/1959 | Snowdown CW | 1 - 2 | Dover | Replay |
| 25/02/1959 | Sittingbourne | 1 - 0 | Folkestone Town | Replay |
| Semi-Final | ||||
| 21/03/1959 | Sittingbourne | 1 - 1 | Canterbury City | |
| 04/04/1959 | Dover | 2 - 2 | Margate | |
| 16/04/1959 | Canterbury City | 0 - 1 | Sittingbourne | Replay |
| 23/04/1959 | Margate | 6 - 0 | Dover | Replay |
| Final | ||||
| 07/05/1959 | Margate | 2 - 3 | Sittingbourne | |
| Preliminary Round | ||||
| 03/09/1958 | Ashford Town Reserves | 2 - 1 | Canterbury City Reserves | |
| 10/09/1958 | Dover Reserves | 0 - 1 | Folkestone Reserves | |
| First Round | ||||
| 10/09/1958 | Margate Reserves | 9 - 1 | Chatham Town Reserves | |
| 11/09/1958 | Sittingbourne Reserves | 4 - 0 | Gillingham A | |
| 18/09/1958 | Herne Bay Reserves | 2 - 2 | Ashford Town Reserves | |
| 20/09/1958 | Tunbridge Wells United Reserves | 2 - 2 | Sheppey United Reserves | |
| 22/09/1958 | Gravesend & Northfleet | 9 - 0 | Whitstable Town Reserves | |
| 24/09/1958 | Ashford Town Reserves | 2 - 5 | Herne Bay Reserves | Replay |
| 25/09/1958 | Ramsgate Athletic Reserves | 2 - 2 | Deal Town Reserves | |
| 25/09/1958 | Faversham Town Reserves | 4 - 0 | Snowdown CW Reserves | |
| 02/10/1958 | Betteshanger CW Reserves | 2 - 2 | Sittingbourne Reserves | |
| 02/10/1958 | Deal Town Reserves | 4 - 3 | Ramsgate Athletic Reserves | Replay |
| 08/10/1958 | Sittingbourne Reserves | 2 - 2 | Betteshanger CW Reserves | Replay |
| 01/11/1958 | Sheppey United Reserves | 2 - 4 | Tunbridge Wells United Reserves | Replay |
| 15/11/1958 | Sittingbourne Reserves | 5 - 1 | Betteshanger CW Reserves | Replay |
| Second Round | ||||
| 29/11/1958 | Faversham Town Reserves | 1 - 0 | Tunbridge Wells United Reserves | |
| 03/12/1958 | Gravesend & Northfleet | 8 - 0 | Deal Town Reserves | |
| 31/12/1958 | Sittingbourne Reserves | - | Folkestone Reserves | |
| 17/01/1959 | Herne Bay Reserves | 2 - 2 | Margate Reserves | |
| 27/03/1959 | Margate Reserves | 3 - 1 | Herne Bay Reserves | Replay |
| Semi-Final | ||||
| 27/03/1959 | Faversham Town Reserves | 1 - 1 | Gravesend & Northfleet | |
| 11/04/1959 | Margate Reserves | 4 - 2 | Sittingbourne Reserves | |
| 18/04/1959 | Gravesend & Northfleet | 5 - 1 | Faversham Town Reserves | Replay |
| Final | ||||
| 09/05/1959 | Margate Reserves | 6 - 3 | Gravesend & Northfleet | |
| First Round | ||||
| 27/12/1958 | Woolwich Poly Reserves | 2 - 1 | Luton (Chatham) Reserves | |
| 27/12/1958 | Dover Reserves | 3 - 0 | Ashford Town Reserves | |
| 03/01/1959 | Maidstone United Reserves | 1 - 3 | Erith & Belvedere Reserves | |
| Second Round | ||||
| 24/01/1959 | Whitstable Town Reserves | p - p | Folkestone Reserves | |
| 24/01/1959 | Sittingbourne Reserves | 7 - 1 | Woolwich Poly Reserves | |
| 24/01/1959 | Sheppey United Reserves | 8 - 0 | Callenders Athletic Reserves | |
| 24/01/1959 | Bexley Reserves | 0 - 5 | Erith & Belvedere Reserves | |
| 24/01/1959 | Dover Reserves | 9 - 1 | Beckenham Reserves | |
| 07/02/1959 | Deal Town Reserves | 2 - 5 | Margate Reserves | |
| 07/02/1959 | Whitstable Town Reserves | 1 - 5 | Folkestone Reserves | |
| 14/02/1959 | Ramsgate Athletic Reserves | 8 - 0 | Brentstonians Reserves | |
| 28/02/1959 | Snowdown CW Reserves | 2 - 1 | Slade Green Athletic Reserves | |
| Quarter-Final | ||||
| 21/02/1959 | Sittingbourne Reserves | 4 - 2 | Sheppey United Reserves | |
| 28/02/1959 | Ramsgate Athletic Reserves | 1 - 0 | Erith & Belvedere Reserves | |
| 28/02/1959 | Folkestone Reserves | 1 - 0 | Margate Reserves | |
| 07/03/1959 | Dover Reserves | 2 - 0 | Snowdown CW Reserves | |
| Semi-Final | ||||
| 30/03/1959 | Ramsgate Athletic Reserves | 0 - 1 | Sittingbourne Reserves | |
| 30/03/1959 | Folkestone Reserves | 2 - 0 | Dover Reserves | |
| Final | ||||
| 25/04/1959 | Folkestone Reserves | 3 - 0 | Sittingbourne Reserves | |