| Wednesday, 22 April 2009 18:45
|
| CAFA Div 1 2009/10 | Castletown | 1 | - | 2 | Halkirk | |
| Wednesday, 29 April 2009 19:00
|
| CAFA Div 1 2009/10 | Castletown | 4 | - | 3 | Wick Rovers | |
| Tuesday, 05 May 2009 19:00
|
| CAFA Div 1 2009/10 | Castletown | 1 | - | 2 | John o Groats | |
| Tuesday, 12 May 2009 19:15
|
| CAFA Div 1 2009/10 | Thurso Pentland | 0 | - | 3 | Castletown | |
| Monday, 18 May 2009 19:15
|
| CAFA Div 1 2009/10 | Castletown | 0 | - | 0 | Pentland United | |
| Tuesday, 26 May 2009 19:15
|
| CAFA Div 1 2009/10 | Wick Groats | 3 | - | 1 | Castletown | |
| Tuesday, 16 June 2009 19:15
|
| CAFA Div 1 2009/10 | Thurso Swifts | 3 | - | 1 | Castletown | |
| Wednesday, 01 July 2009 19:15
|
| CAFA Div 1 2009/10 | Halkirk | 0 | - | 7 | Castletown | |
| Monday, 06 July 2009 19:15
|
| CAFA Div 1 2009/10 | Wick Rovers | 1 | - | 4 | Castletown | |
| Wednesday, 15 July 2009 19:15
|
| CAFA Div 1 2009/10 | John o Groats | 3 | - | 0 | Castletown | |
| Monday, 20 July 2009 19:15
|
| CAFA Div 1 2009/10 | Castletown | 6 | - | 1 | Thurso Pentland | |
| Wednesday, 12 August 2009 19:00
|
| CAFA Div 1 2009/10 | Pentland United | 0 | - | 1 | Castletown | |
| Tuesday, 18 August 2009 19:00
|
| CAFA Div 1 2009/10 | Castletown | 2 | - | 3 | Wick Groats | |
| Monday, 24 August 2009 19:00
|
| CAFA Div 1 2009/10 | Castletown | 3 | - | 0 | Thurso Swifts | |
| Sunday, 30 August 2009 13:00
|
| Cup Games 2009/10 | Wick Groats | 7 | - | 1 | Castletown | |
