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| Last 10 games | more | |||
| 04.09.2008 | CCLQ Preliminary Round | Puerto Rico Islanders | Alajuelense | 2-1 |
| 01.09.2008 | D2 USL1 | Puerto Rico Islanders | Vancouver Whitecaps | 1-1 |
| 30.08.2008 | D2 USL1 | Charleston Battery | Puerto Rico Islanders | 0-0 |
| 28.08.2008 | CCLQ Preliminary Round | Alajuelense | Puerto Rico Islanders | 1-1 |
| 23.08.2008 | D2 USL1 | Puerto Rico Islanders | Charleston Battery | 2-1 |
| 18.08.2008 | D2 USL1 | Vancouver Whitecaps | Puerto Rico Islanders | 0-0 |
| 16.08.2008 | D2 USL1 | Seattle Sounders | Puerto Rico Islanders | 0-3 |
| 11.08.2008 | D2 USL1 | Rochester Raging Rhinos | Puerto Rico Islanders | 1-1 |
| 09.08.2008 | D2 USL1 | Puerto Rico Islanders | Rochester Raging Rhinos | 4-0 |
| 04.08.2008 | D2 USL1 | Puerto Rico Islanders | Carolina Railhawks | 1-0 |
| Next 10 games | more | |||
| 06.09.2008 | D2 USL1 | Puerto Rico Islanders | Vancouver Whitecaps |  |
| 13.09.2008 | D2 USL1 | Rochester Raging Rhinos | Puerto Rico Islanders | |
| 17.09.2008 | D2 USL1 | Montreal Impact | Puerto Rico Islanders | |
| 20.09.2008 | D2 USL1 | Puerto Rico Islanders | Atlanta Silverbacks | |