| Date | Team | Opposition | Start | Location | Type | ||
|---|---|---|---|---|---|---|---|
| Sun 18th April 1999 | Sunday 2nds - Friendly | v | Coleshill | Away | Friendly | Away (Friendly) | |
| Sun 25th April 1999 | Sunday 2nds - Friendly | v | Southgate | Away | Friendly | Away (Friendly) | |
| Sun 2nd May 1999 | Sunday 2nds - Friendly | v | Farnham Royal | The Common | Friendly | The Common (Friendly) | |
| Sun 9th May 1999 | Sunday 2nds - Friendly | v | London Colney | Away | Friendly | Away (Friendly) | |
| Sun 16th May 1999 | Sunday 2nds - Friendly | v | Stanmore | The Common | Friendly | null - The Common (Friendly) | |
| Sun 23rd May 1999 | Sunday 2nds - Friendly | v | Elstree | Away | Conference | Away (Conference) | |
| Sun 30th May 1999 | Sunday 2nds - Friendly | v | Carpenters Arms | The Common | Friendly | null - The Common (Friendly) | |
| Sun 6th June 1999 | Sunday 2nds - Friendly | v | Botany Bay | Away | Conference | Away (Conference) | |
| Sun 13th June 1999 | Sunday 2nds - Friendly | v | Hatfield | Away | Conference | Away (Conference) | |
| Sun 20th June 1999 | Sunday 2nds - Friendly | v | Harpenden | The Common | Conference | The Common (Conference) | |
| Sun 27th June 1999 | Sunday 2nds - League | v | Abbots Langley | The Common | CV | The Common (CV) | |
| Sun 4th July 1999 | Sunday 2nds - Friendly | v | Little Kingshill | Away | Conference | Away (Conference) | |
| Sun 11th July 1999 | Sunday 2nds - League | v | Berkhamsted | Away | CV | Away (CV) | |
| Sun 18th July 1999 | Sunday 2nds - Friendly | v | Northwood | Away | Friendly | Away (Friendly) | |
| Sun 25th July 1999 | Sunday 2nds - Friendly | v | Berkhamsted | The Common | Friendly | The Common (Friendly) | |
| Sun 1st August 1999 | Sunday 2nds - League | v | Radlett | Away | CV | Away (CV) | |
| Sun 8th August 1999 | Sunday 2nds - Friendly | v | Langleybury | The Common | Friendly | null - The Common (Friendly) | |
| Sun 15th August 1999 | Sunday 2nds - League | v | Chenies & Latimer | The Common | CV | The Common (CV) | |
| Sun 22nd August 1999 | Sunday 2nds - League | v | Amersham Hill | The Common | CV | null - The Common (CV) | |
| Sun 5th September 1999 | Sunday 2nds - Friendly | v | Harpenden | Away | Friendly | Away (Friendly) | |
| Sun 12th September 1999 | Sunday 2nds - Friendly | v | Chipperfield | Away | Friendly | Away (Friendly) |