Season 2008/09 This season see's the return of Frank Rowberry who I am sure will bring back the enthusiasm to the players in there quest for honors. Frank has already started training the 3rd team on there own dedicated training night (Wednesdays). Good Luck for the season.
Season 2007/08 saw the 3rd team finish 4th in the league and with no silverware in any of the cups to show for the teams efforts.
Season 2006/07 saw Caldicot finish in 3rd place, there highest position for some years. The 3rd team were also successful in winning the inaugural "Floodlit Cup Competition" and came runners-up in the Watkin Shield Final.
Fixtures/Results/Scorers 2010/11
| Fixture | Date | Venue | Result | Scorer(s) |
| Monmouth Town | 2 Sep | Away | W 2-0 | Light 1, Bright 1 |
| Chepstow Town | 4 Sep | Home | L 1-0 | |
| Rockfield Rovers | 11 Sep | Home | W 9-2 | S.Jeremiah 5, L.Jeremiah 1, R.Jeremiah 1, J.Reed 2 |
| Chepstow Ath | 25 Sep | Home | W 5-0 | Ben cup - Caldicot awarded win |
| Underwood | 02 Oct | Away | D 2-2 | M.Williamson 1, J.Watts 1 |
| Undy "A" | 09 Oct | Away | L 4-1 | T.Boston |
| Chepstow Town | 23 Oct | Away | L 3-2 | M.Addis 1, N.Murphy 1 |
| Rockfield - Gill Cup | 30 Oct | Home | W 9-1 | S.Jeremiah 2, L.Jeremiah 2, J.Reed 2, A.Jones 1 M.Williamson 1, D.Haywood 1 |
| New Inn -Amatuer Cup | 06 Nov | Home | L 5-2 | A.Watkins 1, T.Moore 1 |
Fixtures/Results/Scorers 2009/10
| August Fixtures | ||
| Caldicot Town "A" v Tintern Abbey | W 3-0 | S.Jeremiah 1, T.Jones 1, P.Light 1 |
| Caldicot Town "A" v Caldicot Castle | W 8-0 | P.Light 1, S.Jeremiah 3, R.Jeremiah 1, M.Beresford 1 L.Moreton 1, M.Williamson 1 |
| September Fixtures | ||
| Undy Ath "A" v Caldicot Town "A" | L 3-2 | S.Crook 1, P.Light 1 |
| Caldicot Town "A" v Rockfield Rovers | W 9-0 | S.Jeremiah 3, R.Jeremiah 2, P.Light 1, A.Porter 1, S.McKeon 1, M.Williamson 1 |
| Chepstow Town v Caldicot Town "A" | L 5-4 | D.Smith 2, M.Beresford 1, L.Jeremiah 1 |
| Wyesham Wan v Caldicot Town "A" | P-P | |
| Caldicot Town "A" v Sudbrook "A" | W 10-2 | P.Light 3, S.Jeremiah 3, J.Lawrence 1, M.Beresford 1 S.McKeon 2 |
| October Fixtures | ||
| Caldicot Castle v Caldicot Town "A" | W11-0 | P.Light 2, A.Watkins 2, R.Bailey 2, T.Moore 1, L.Moreton 1, J.Lawrence 1, A.Porter 1, M.Beresford 1 |
Caldicot Town "A" v Caldicot Castle "A" Gill Cup | W 7-1 | P.Light 3, L.Jeremiah 3, M.Beresford 1 |
| Caldicot Town v Undy Athletic | L 2-1 | A.Jones 1 |
| Caldicot Town v Wyesham Wanderers | W 3-0 | P.Light 1, L.Jeremiah 1, M.Williamson 1 |
| November Fixtures | ||
| Caldicot Town v Undy Athletic | W 2-0 | P.Light 1, L.Jeremiah 1 |
Caldicot Town v Chepstow Town Ben Cup Round One | L 8-4 | P.Light 2, S.Crook 1, J.Reed 1 |
| December Fixtures | ||
| Rockfield Rovers v Caldicot Town | W 6-1 | P.Light 3, S.Jeremiah 3 |
| January Fixtures | ||
| Chepstow Town v Caldicot Town | P-P | |
| Sudbrook CC v Caldicot Town | P-P | |
| Caldicot Town v Sudbrook CC | W 4-1 | P.Light 1, T.Moore 1, A.Porter 1, M.Williamson 1 |
| Caldicot Town v Rockfield Rovers | W 1-0 | P.Light 1 |
| Caldicot Town v Caldicot Castle | W 3-0 | P.Light 2, A.Jones 1 |
| February Fixtures | ||
| Sudbrook "A" v Caldicot "A" | P-P | |
| Caldicot "A" v Chepstow Town "A" | L 4-3 | S.McKeon 1,P.Light 1, R.Guscott 1 |
| Wyesham "A" v Caldicot "A" | W11-2 | P.Light 3, D.Smith 3, S.Jeremiah 3, A.Porter 1, L.Jeremiah 1 |
| Chepstow Town "A" v Caldicot "A" | P-P | |
| March Fixtures | ||
| Caldicot v Tintern | L 3-0 | |
| Caldicot v Tintern - Gill Cup Semi | W 4-2 | J.Lawrence 1, J.McKeon 1, L.Moreton 1, S.Jeremiah 1 |
| Sudbrook "A" v Caldicot "A" | W 5-0 | M.Slape 2, J.McGinty 2, A.Bundock |
| Wyesham "A" v Caldicot "A" | W 6-1 | TBC |
| Tintern v Caldicot @ Caldicot | D 1-1 | N.Murphy 1 |
| Caldicot v Sudbrook Gill Cup Final | W 3-2 | S.Crook 1, J.McKeon 1, P.Light 1 |
| Chepstow v Caldicot | W 5-0 | S.Crook 1, J.McKeon 1, B.Miles 1, P.Light 2 |
GILL Cup Final Winners 2009/2010
