| Game | Date | Time | Field | Visitor | Home | Box Scores |
| 1 | Sunday, May 03, 2009 | 6:00:00 PM | Exhibition - Millcroft 'C' ** | Cardinals | Cubs | 0 - 0 ( ) |
| 2 | Tuesday, May 05, 2009 | 8:30:00 PM | Exhibition - Millcroft 'B' ** | Cubs | Giants | 0 - 0 ( ) |
| 3 | Friday, May 08, 2009 | 6:00:00 PM | Millcroft 'C' ** | Cubs | X-Men | 7 - 6 (W) |
| 4 | Sunday, May 24, 2009 | 6:00:00 PM | Nelson | X-Men | Cubs | PPD - LSGC |
| 5 | Sunday, May 31, 2009 | 6:00:00 PM | Ireland 'C' | Cubs | Marauders | 7 - 4 (L) |
| 6 | Friday, June 05, 2009 | 8:30:00 PM | Ireland 'C' | X-Men | Cubs | 9 - 5 (W) |
| 7 | Sunday, June 07, 2009 | 8:30:00 PM | Nelson | Cubs | Tigers | 18 - 5 (L) |
| 8 | Tuesday, June 09, 2009 | 6:00:00 PM | Nelson | Cubs | Mud Hens | 3 - 2 (L) |
| 9 | Friday, June 12, 2009 | 6:00:00 PM | Nelson - Rescheduled from 05/24 | X-Men | Cubs | 12 - 5 (W) |
| 10 | Friday, June 19, 2009 | 8:30:00 PM | Nelson | Giants | Cubs | 7 - 5 (L) |
| 11 | Sunday, June 21, 2009 | 6:00:00 PM | Nelson | Cubs | Brewers | 12 - 5 (L) |
| 12 | Tuesday, June 23, 2009 | 6:00:00 PM | Nelson | Cubs | Red Sox | 8 - 6 (W) |
| 13 | Sunday, July 05, 2009 | 8:30:00 PM | Nelson | Marauders | Cubs | 9 - 4 (L) |
| 14 | Friday, July 10, 2009 | 6:00:00 PM | Nelson | Cubs | Giants | 3 - 2 (W) |
| 15 | Sunday, July 12, 2009 | 6:00:00 PM | Ireland 'C' | Tigers | Cubs | 8 - 0 (L) |
| 16 | Friday, July 17, 2009 | 6:00:00 PM | Ireland 'C' | Mud Hens | Cubs | 6 - 2 (L) |
| 17 | Sunday, July 19, 2009 | 8:30:00 PM | Ireland 'C' | Hobos | Cubs | 6 - 1 (L) |
| 18 | Friday, July 24, 2009 | 6:00:00 PM | Nelson | Cubs | Cardinals | 14 - 12 (L) |
| 19 | Sunday, July 26, 2009 | 8:30:00 PM | Nelson | Cubs | X-Men | PPD Rain |
| 20 | Friday, August 07, 2009 | 6:00:00 PM | Ireland 'C' | Cardinals | Cubs | 15 - 5 (L) |
| 21 | Sunday, August 09, 2009 | 8:30:00 PM | Ireland 'C' | Brewers | Cubs | PPD Rain |
| 22 | Tuesday, August 11, 2009 | 6:00:00 PM | Nelson | Cubs | Hobos | 9 - 4 (L) |
| 23 | Friday, August 21, 2009 | 8:30:00 PM | Nelson | Red Sox | Cubs | 13 - 1 ( ) |
| 24 | Sunday, August 23, 2009 | 8:30:00 PM | Nelson - Rescheduled from 07/26 | Cubs | X-Men | 10 - 4 (W) |
| 25 | Tuesday, August 25, 2009 | 8:30:00 PM | Nelson - Rescheduled from 08/09 | Brewers | Cubs | 0 - 0 ( ) |
| 26 | End of Regular Season | |||||
| 27 | ||||||
| 28 | ** Park Change - Updated April 13, 2009 |