| Monday, 20 April 2009 18:45
|
| CAFA Div 1 2009/10 | Pentland United | 4 | - | 0 | Thurso Pentland | |
| Tuesday, 28 April 2009 19:00
|
| CAFA Div 1 2009/10 | John o Groats | 0 | - | 3 | Pentland United | |
| Monday, 04 May 2009 19:00
|
| CAFA Div 1 2009/10 | Pentland United | 4 | - | 0 | Wick Rovers | |
| Tuesday, 12 May 2009 19:15
|
| CAFA Div 1 2009/10 | Halkirk | 1 | - | 2 | Pentland United | |
| 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 | Pentland United | 1 | - | 1 | Thurso Swifts | |
| Saturday, 30 May 2009 15:00
|
| Cup Games 2009/10 | Pentland United | 1 | - | 2 | Wick Groats | |
| Tuesday, 16 June 2009 19:15
|
| CAFA Div 1 2009/10 | Pentland United | 0 | - | 1 | Wick Groats | |
| Monday, 29 June 2009 19:15
|
| CAFA Div 1 2009/10 | Thurso Pentland | 2 | - | 3 | Pentland United | |
| Tuesday, 07 July 2009 19:15
|
| CAFA Div 1 2009/10 | Pentland United | 1 | - | 2 | John o Groats | |
| Wednesday, 15 July 2009 19:15
|
| CAFA Div 1 2009/10 | Wick Rovers | 3 | - | 2 | Pentland United | |
| Monday, 20 July 2009 19:15
|
| CAFA Div 1 2009/10 | Pentland United | 1 | - | 2 | Halkirk | |
| Wednesday, 12 August 2009 19:00
|
| CAFA Div 1 2009/10 | Pentland United | 0 | - | 1 | Castletown | |
| Monday, 17 August 2009 19:00
|
| CAFA Div 1 2009/10 | Thurso Swifts | 3 | - | 1 | Pentland United | |
| Monday, 24 August 2009 19:00
|
| CAFA Div 1 2009/10 | Wick Groats | 1 | - | 1 | Pentland United | |