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| Last 10 games | more | |||
| 13.10.2008 | D2PO Playoff Final | Vancouver Whitecaps | Puerto Rico Islanders | 2-1 |
| 09.10.2008 | CCL Group D | Santos Laguna | Puerto Rico Islanders | 3-0 |
| 06.10.2008 | D2PO Playoff Semifinal | Puerto Rico Islanders | Rochester Raging Rhinos | 3-0 AET |
| 04.10.2008 | D2PO Playoff Semifinal | Rochester Raging Rhinos | Puerto Rico Islanders | 2-0 |
| 02.10.2008 | CCL Group D | Municipal | Puerto Rico Islanders | 2-2 |
| 24.09.2008 | CCL Group D | Puerto Rico Islanders | Santos Laguna | 3-1 |
| 22.09.2008 | D2 USL1 | Montreal Impact | Puerto Rico Islanders | 0-0 |
| 20.09.2008 | D2 USL1 | Puerto Rico Islanders | Atlanta Silverbacks | 1-1 |
| 17.09.2008 | CCL Group D | Puerto Rico Islanders | Tauro FC | 2-1 |
| 13.09.2008 | D2 USL1 | Rochester Raging Rhinos | Puerto Rico Islanders | 0-2 |
| Next 10 games | more | |||
| 23.10.2008 | CCL Group D | Puerto Rico Islanders | Municipal |  |
| 29.10.2008 | CCL Group D | Tauro FC | Puerto Rico Islanders | |