| Saturday, 30 May 2009 13:00
|
| HDCL REGULAR SEASON | Oakville Cricket Club | 120 | - | 123 | Hamilton Cricket Club | |
| Sunday, 31 May 2009 13:00
|
| HDCL REGULAR SEASON | Mississauga Ramblers Cricket Club | 207 | - | 175 | Oakville Cricket Club | |
| Sunday, 07 June 2009 13:00
|
| HDCL REGULAR SEASON | Oakville Cricket Club | 81 | - | 228 | Cambridge Cricket Club | |
| Saturday, 13 June 2009 13:00
|
| HDCL REGULAR SEASON | Crescent Colts | 201 | - | 130 | Oakville Cricket Club | |
| Saturday, 20 June 2009 13:00
|
| ED BURN 20/20 | Cambridge Cricket Club | | - | | Oakville Cricket Club | |
| Sunday, 21 June 2009 09:30
|
| ED BURN 20/20 | Mississauga Ramblers Cricket Club | | - | | Oakville Cricket Club | |
| Sunday, 21 June 2009 16:30
|
| ED BURN 20/20 | Oakville Cricket Club | 111 | - | 110 | Crescent Colts | |
| Wednesday, 01 July 2009 09:30
|
Churchill Park | ED BURN 20/20 | Hamilton Cricket Club | 103 | - | 102 | Oakville Cricket Club | |
| Sunday, 05 July 2009 13:00
|
| HDCL REGULAR SEASON | Oakville Cricket Club | 82 | - | 81 | Mississauga Ramblers Cricket Club | |
| Saturday, 18 July 2009 13:00
|
| ED BURN 20/20 | Oakville Cricket Club | 150 | - | 152 | Halton Stars Cricket Club | |
| Sunday, 19 July 2009 13:00
|
Avebury Grounds | ED BURN 20/20 | Cambridge Cricket Club | 97 | - | 107 | Oakville Cricket Club | |
| Saturday, 08 August 2009 13:00
|
| HDCL REGULAR SEASON | Oakville Cricket Club | 10 | - | 0 | Crescent Colts | |
| Saturday, 08 August 2009 13:00
|
Churchill Park | HDCL REGULAR SEASON | Hamilton Cricket Club | | - | | Oakville Cricket Club | |
| Sunday, 09 August 2009 13:00
|
| HDCL REGULAR SEASON | Cambridge Cricket Club | | - | | Oakville Cricket Club | |
| Saturday, 15 August 2009 16:30
|
| ED BURN 20/20 | Mississauga Ramblers Cricket Club | 140 | - | 105 | Oakville Cricket Club | |
| Saturday, 22 August 2009 13:00
|
| HDCL REGULAR SEASON | Oakville Cricket Club | 129 | - | 67 | St.Catharines Cricket Club | |
| Saturday, 29 August 2009 13:00
|
| HDCL REGULAR SEASON | Mississauga Colts | 38 | - | 39 | Oakville Cricket Club | |
| Saturday, 05 September 2009 13:00
|
| HDCL REGULAR SEASON | Hamilton Colts | 161 | - | 162 | Oakville Cricket Club | |
| Saturday, 12 September 2009 13:00
|
| HDCL REGULAR SEASON | Crescent Cricket Club | 222 | - | 223 | Oakville Cricket Club | |
