| Date | Team | Opposition | Start | Location | Type | ||
|---|---|---|---|---|---|---|---|
| Sun 23rd April 2000 | Sunday 1sts - Friendly | v | Sandridge | The Common | Friendly | null - The Common (Friendly) | |
| Sunday 2nds - Friendly | v | Ley Hill | Away | Friendly | null - Away (Friendly) | ||
| Sat 29th April 2000 | Saturday 1sts - Friendly | v | Old Merchant Taylors | The Common | Friendly | null - The Common (Friendly) | |
| Saturday 2nds - Friendly | v | Old Merchant Taylors | Away | Friendly | null - Away (Friendly) | ||
| Sun 30th April 2000 | Sunday 1sts - Friendly | v | Southgate | Away | Friendly | null - Away (Friendly) | |
| Sunday 2nds - Friendly | v | Southgate | The Common | Friendly | The Common (Friendly) | ||
| Mon 1st May 2000 | Sunday 1sts - Friendly | v | Clarendon | The Common | Friendly | The Common (Friendly) | |
| Sat 6th May 2000 | Saturday 3rds - Friendly | v | Coopers | Away | Friendly | Away (Friendly) | |
| Saturday 1sts - League | v | Radlett 2 | Away | HL | Away (HL) | ||
| Saturday 2nds - League | v | Reed 1 | The Common | HL | The Common (HL) | ||
| Sun 7th May 2000 | Sunday 1sts - Friendly | v | Farnham Royal | The Common | Friendly | The Common (Friendly) | |
| Sunday 2nds - Friendly | v | Farnham Royal | Away | Friendly | Away (Friendly) | ||
| Sat 13th May 2000 | Saturday 3rds - Friendly | v | Broxbourne | Away | Friendly | Away (Friendly) | |
| Saturday 1sts - League | v | Old Millhillians 1 | Away | HL | Away (HL) | ||
| Saturday 2nds - League | v | Old Haberdashers 1 | The Common | HL | The Common (HL) | ||
| Sun 14th May 2000 | Sunday 1sts - Friendly | v | London Colney | Away | Friendly | Away (Friendly) | |
| Sunday 2nds - Friendly | v | London Colney | The Common | Friendly | The Common (Friendly) | ||
| Sat 20th May 2000 | Saturday 1sts - League | v | Hitchin 1 | Away | HL | Away (HL) | |
| Saturday 2nds - League | v | Wheathampstead 2 | The Common | HL | The Common (HL) | ||
| Saturday 3rds - League | v | Southgate Adelaide 3 | Westwood Park | HL | Westwood Park (HL) | ||
| Sun 21st May 2000 | Sunday 1sts - Friendly | v | Stanmore | The Common | Friendly | null - The Common (Friendly) | |
| Sunday 2nds - Friendly | v | Stanmore | Away | Friendly | null - Away (Friendly) | ||
| Sat 27th May 2000 | Saturday 1sts - League | v | Chipperfield 1 | The Common | HL | The Common (HL) | |
| Saturday 2nds - League | v | Dunstable Town 2 | Away | HL | null - Away (HL) | ||
| Saturday 3rds - League | v | Langleybury 4 | Westwood Park | HL | null - Westwood Park (HL) | ||
| Sun 28th May 2000 | Sunday 1sts - Friendly | v | Bishop's Stortford | The Common | Friendly | null - The Common (Friendly) | |
| Sunday 2nds - Friendly | v | Chipperfield | Away | Friendly | null - Away (Friendly) | ||
| Mon 29th May 2000 | Sunday 1sts - Friendly | v | Amersham | Away | Friendly | Away (Friendly) | |
| Sat 3rd June 2000 | Saturday 1sts - League | v | Dunstable Town 1 | Away | HL | Away (HL) | |
| Saturday 2nds - League | v | Bushey 1 | The Common | HL | The Common (HL) | ||
| Saturday 3rds - League | v | Old Camdenians 3 | Westwood Park | HL | Westwood Park (HL) | ||
| Sun 4th June 2000 | Sunday 1sts - Friendly | v | Langleybury | The Common | Friendly | The Common (Friendly) | |
| Sunday 2nds - Friendly | v | Carpenters Arms | Away | Friendly | Away (Friendly) | ||
| Sat 10th June 2000 | Saturday 3rds - Friendly | v | Old Manorians | Away | Friendly | Away (Friendly) | |
| Saturday 1sts - League | v | Potters Bar 1 | Away | HL | Away (HL) | ||
| Saturday 2nds - League | v | Boxmoor 1 | The Common | HL | The Common (HL) | ||
| Sun 11th June 2000 | Sunday 1sts - Friendly | v | Bishop's Stortford | The Common | Friendly | The Common (Friendly) | |
| Sunday 2nds - Friendly | v | Hexton | Away | Friendly | Away (Friendly) | ||
| Wed 14th June 2000 | Sunday 1sts - Friendly | v | Gentlemen of Herts | The Common | Friendly | null - The Common (Friendly) | |
| Sat 17th June 2000 | Saturday 1sts - League | v | Welwyn Garden City 1 | Away | HL | Away (HL) | |
| Saturday 2nds - League | v | UCA 1 | The Common | HL | The Common (HL) | ||
| Saturday 3rds - League | v | Cheshunt 2 | Westwood Park | HL | Westwood Park (HL) | ||
| Sun 18th June 2000 | Sunday 1sts - League | v | Boxmoor | The Common | CV | The Common (CV) | |
| Sunday 2nds - League | v | Abbots Langley | Away | CV | Away (CV) | ||
| Sat 24th June 2000 | Saturday 1sts - League | v | Leverstock Green 1 | The Common | HL | The Common (HL) | |
| Saturday 2nds - League | v | Northwood Town 1 | Away | HL | Away (HL) | ||
| Saturday 3rds - League | v | Botany Bay 3 | Away | HL | Away (HL) | ||
| Sun 25th June 2000 | Sunday 1sts - Friendly | v | Chenies & Latimer | The Common | Friendly | The Common (Friendly) | |
| Sunday 2nds - Friendly | v | Chenies & Latimer | Away | Friendly | Away (Friendly) | ||
| Sat 1st July 2000 | Saturday 1sts - League | v | Sawbridgeworth 1 | Away | HL | Away (HL) | |
| Saturday 2nds - League | v | Northampton Exiles 1 | The Common | HL | The Common (HL) | ||
| Saturday 3rds - League | v | Ibis 1 | Westwood Park | HL | Westwood Park (HL) | ||
| Sun 2nd July 2000 | Sunday 1sts - League | v | Harpenden | The Common | CV | The Common (CV) | |
| Sunday 2nds - League | v | Amersham Hill | Away | CV | Away (CV) | ||
| Sat 8th July 2000 | Saturday 1sts - League | v | Radlett 2 | The Common | HL | The Common (HL) | |
| Saturday 2nds - League | v | North Mymms 2 | Away | HL | Away (HL) | ||
| Saturday 3rds - League | v | Two Woods 1 | Away | HL | Away (HL) | ||
| Sun 9th July 2000 | Sunday 1sts - Friendly | v | Royal Ascot | Away | Friendly | Away (Friendly) | |
| Sunday 2nds - Friendly | v | Moor Park Golf Club | The Common | Friendly | null - The Common (Friendly) | ||
| Sat 15th July 2000 | Saturday 1sts - League | v | Old Millhillians 1 | The Common | HL | The Common (HL) | |
| Saturday 2nds - League | v | Bayford & Hertford 1 | Away | HL | Away (HL) | ||
| Saturday 3rds - League | v | Northampton Exiles 3 | Westwood Park | HL | Westwood Park (HL) | ||
| Sun 16th July 2000 | Sunday 1sts - League | v | Kenton | Away | CV | Away (CV) | |
| Sunday 2nds - League | v | Hemel Hempstead | The Common | CV | The Common (CV) | ||
| Mon 17th July 2000 | Kent Tour | v | Sibton Park | Away | Tour | Away (Tour) | |
| Tue 18th July 2000 | Kent Tour | v | Hastings & St Leonard's Priory | Away | Tour | Away (Tour) | |
| Wed 19th July 2000 | Kent Tour | v | Tenterden | Away | Tour | Away (Tour) | |
| Thu 20th July 2000 | Kent Tour | v | Linden Park | Away | Tour | Away (Tour) | |
| Sat 22nd July 2000 | Saturday 1sts - League | v | Hitchin 1 | The Common | HL | The Common (HL) | |
| Saturday 2nds - League | v | Berkhamsted 2 | Away | HL | Away (HL) | ||
| Saturday 3rds - League | v | Kings Langley 3 | Westwood Park | HL | Westwood Park (HL) | ||
| Sun 23rd July 2000 | Sunday 1sts - Friendly | v | Northwood | The Common | Friendly | null - The Common (Friendly) | |
| Sunday 2nds - Friendly | v | Northwood | Away | Friendly | Away (Friendly) | ||
| Fri 28th July 2000 | Sunday 1sts - Friendly | v | Ockbrook and Burrowash | The Common | Friendly | null - The Common (Friendly) | |
| Sat 29th July 2000 | Saturday 1sts - League | v | Chipperfield 1 | Away | HL | Away (HL) | |
| Saturday 2nds - League | v | Braughing 1 | The Common | HL | The Common (HL) | ||
| Saturday 3rds - League | v | Leverstock Green 3 | Westwood Park | HL | Westwood Park (HL) | ||
| Sun 30th July 2000 | Sunday 1sts - League | v | Houghton Town | The Common | CV | The Common (CV) | |
| Sunday 2nds - League | v | Radlett | Away | CV | Away (CV) | ||
| Sat 5th August 2000 | Saturday 1sts - League | v | Dunstable Town 1 | The Common | HL | The Common (HL) | |
| Saturday 2nds - League | v | Redbourn 1 | Away | HL | Away (HL) | ||
| Saturday 3rds - League | v | Aldenham | Westwood Park | HL | Westwood Park (HL) | ||
| Sun 6th August 2000 | Sunday 1sts - Friendly | v | Bucks | Away | Friendly | Away (Friendly) | |
| Sunday 1sts - League | v | Leverstock Green | Away | CV | Away (CV) | ||
| Sunday 2nds - League | v | North Mymms | The Common | CV | The Common (CV) | ||
| Sat 12th August 2000 | Saturday 1sts - League | v | Potters Bar 1 | The Common | HL | The Common (HL) | |
| Saturday 2nds - League | v | Hatfield Hyde 1 | Away | HL | Away (HL) | ||
| Saturday 3rds - League | v | Northwood 3 | Away | HL | Away (HL) | ||
| Sun 13th August 2000 | Sunday 1sts - Friendly | v | Berkhamsted | Away | Friendly | Away (Friendly) | |
| Sunday 2nds - Friendly | v | Berkhamsted | The Common | Friendly | The Common (Friendly) | ||
| Sat 19th August 2000 | Saturday 1sts - League | v | Welwyn Garden City 1 | Away | HL | Away (HL) | |
| Saturday 2nds - League | v | Old Millhillians 2 | The Common | HL | The Common (HL) | ||
| Saturday 3rds - League | v | Rising Stars | Westwood Park | HL | Westwood Park (HL) | ||
| Sun 20th August 2000 | Sunday 1sts - Friendly | v | Hillingdon | The Common | Friendly | The Common (Friendly) | |
| Sunday 2nds - League | v | Northwood Town | Away | CV | null - Away (CV) | ||
| Sat 26th August 2000 | Saturday 1sts - League | v | Leverstock Green 1 | Away | HL | null - Away (HL) | |
| Saturday 2nds - League | v | Sawbridgeworth 2 | The Common | HL | null - The Common (HL) | ||
| Saturday 3rds - League | v | Hatfield 3 | Away | HL | null - Away (HL) | ||
| Sun 27th August 2000 | Sunday 1sts - Friendly | v | Stage | The Common | Friendly | The Common (Friendly) | |
| Mon 28th August 2000 | Strollers XI | v | Cublington | The Common | Friendly | The Common (Friendly) | |
| Sat 2nd September 2000 | Saturday 1sts - League | v | Sawbridgeworth 1 | The Common | HL | The Common (HL) | |
| Saturday 2nds - League | v | Sandridge 1 | Away | HL | Away (HL) | ||
| Sun 3rd September 2000 | Sunday 2nds - Friendly | v | Aldenham | The Common | Friendly | The Common (Friendly) | |
| Sunday 1sts - League | v | Mill Hill Village | Away | CV | Away (CV) | ||
| Sat 9th September 2000 | Sunday 1sts - Friendly | v | Flamstead | The Common | Friendly | The Common (Friendly) | |
| Saturday 2nds - League | v | Ampthill Town 1 | Away | HL | Away (HL) | ||
| Sun 10th September 2000 | Sunday 1sts - Friendly | v | Harpenden | Away | Friendly | Away (Friendly) | |
| Sunday 2nds - Friendly | v | Harpenden | The Common | Friendly | The Common (Friendly) | ||
| Sat 16th September 2000 | Saturday 1sts - Friendly | v | North London | The Common | Friendly | null - The Common (Friendly) | |
| Saturday 2nds - Friendly | v | North London | Away | Friendly | null - Away (Friendly) | ||
| Sun 17th September 2000 | Sunday 1sts - Friendly | v | Kings Langley | The Common | Friendly | null - The Common (Friendly) | |
| Sunday 2nds - Friendly | v | Berkhamsted | Away | Friendly | Away (Friendly) | ||
| Strollers XI | v | Red Lion | The Common | Friendly | The Common (Friendly) | ||
| Sat 23rd September 2000 | Sunday 1sts - Friendly | v | Abbots Langley | Away | Friendly | Away (Friendly) | |
| Saturday 2nds - Friendly | v | Abbots Langley | The Common | Friendly | null - The Common (Friendly) | ||
| Sun 24th September 2000 | Sunday 1sts - Friendly | v | Sarratt | The Common | Friendly | null - The Common (Friendly) | |
| Sat 30th September 2000 | Sunday 1sts - Friendly | v | Amersham Hill | The Common | Friendly | The Common (Friendly) |