| 2008 | Activity | Venue |
| Sun 7th September | WBS:
Kings South Coast 15s Tournament | |
| Wed 10th September | WBS:
1stXV v Sir William Borlaise | Away
2.15pm |
| Sun 14th September | | |
| Wed 17th September | U18 Daily Mail Cup (R1) | |
| Sat 20th September | WBS:
1stXV v Aylesbury GS
2ndXV v Aylesbury GS |
Away
10.30am |
| Sun 21st September | Windsor Youth Registration
OBB Colts League
Windsor v Newbury | Home |
| Thu 25th September | WBS:
1stXV v Eton | Away
4.30pm |
| Sat 27th September | WBS:
1stXV v St Bartholomews
2ndXV v St Bartholomews |
Away
10.30am |
| Sun 28th September | County U18s Training/Selection | |
| Wed 1st October | U18 Daily Mail Cup (R2) | |
| Thu 2nd October | WBS:
2ndXV v Eton | Away
4.30pm |
| Sat 4th October | WBS:
1stXV v Reading School | Home
10.30am |
| Sun 5th October | Windsor Minis Tournament | |
| Mon 6th October | County U18s v Oxon | Away |
| Wed 8th October | WBS:
1stXV v Forest/Kennet | Home
2.30pm |
| Sat 11th October | WBS:
1stXV v Hampton
2ndXV v Hampton |
Away
10.30am |
| Sun 12th October | Windsor Juniors Tournament | |
| Wed 15th October | U18 Daily Mail Cup (R3/V1) | |
| Sat 18th October | WBS:
1stXV v Tiffin
2ndXV v Tiffin |
Away
10.30am |
| Sun 26th October | County U18s v Dorset & Wilts | Home |
| Wed 29th October | County U18s Training | |
| Sun 2nd November | County U18s v Bucks | Away |
| Wed 5th November | U18 Daily Mail Cup (V2)
WBS:
1stXV v Shiplake
2ndXV v Shiplake |
Home
2.30pm |
| Sun 9th November | OBB Colts League
Windsor v Redingensians | Home |
| Wed 12th November | U18 Daily Mail Cup (R4/V3) | |
| Sat 15th November | WBS:
1stXV v St Benedicts
2ndXV v St Benedicts |
Home
10.30am |
| Sun 23rd November | U18s South West Trials | |
| Wed 26th November | U18 Daily Mail Cup (R5/V4) | |
| Sat 29th November | WBS:
1stXV v Reading Blue Coats
2ndXV v Reading Blue Coats |
Home
10.30am |
| Sun 30th November | OBB Colts League
Amersham & Chiltern v Windsor | Away |
| Wed 3rd December | WBS:
1stXV v Desborough
2ndXV v Desborough |
Home
2.15pm |
| Sat 6th December | WBS:
1stXV v Claires Court
2ndXV v Claires Court |
Home
10.30am |
| Wed 10th December | U18 Daily Mail Cup (R6/V5)
WBS:
1stXV v St Georges
2ndXV v St Georges |
Home
2.30pm |
| Sun 14th December | OBB U17s League
Witney v Windsor | Away |
| Sun 21st December |
CHRISTMAS | |
| Sun 28th December | CHRISTMAS | |
| 2009 | | |
| Sun 4th January | OBB Colts League
Windsor v Reading Abbey | Home |
| Sun 11th January | | |
| Wed 14th January | U18 Daily Mail Cup (V6) | |
| Sun 18th January | | |
| Wed 21st January | U18 Daily Mail Cup (R7/V7) | |
| Sun 25th January | | |
| Sun 1st February | | |
| Sun 8th February | | |
| Wed 11th February | U18 Daily Mail Cup (QF) | |
| Sun 15th February | | |
| Sun 22nd February | | |
| Wed 25th February | U18 Daily Mail Cup (SF) | |
| Sun 1st March | | |
| Sun 8th March | | |
| Sun 15th March | | |
| Sun 22nd March | | |
| Wed 25th March | U18 Daily Mail Cup (Final) | |
| Sun 29th March | | |
| Sun 5th April | | |
| Sun 12th April | EASTER | |
| Sun 19th April | | |
| Sun 26th April | | |
| Sun 3rd May | | |
