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| Saturday, December 20, 2008 Field 3 | ||||
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3:00 pm | Gold Star Soccer | at VSA 1 | |
| Saturday, December 27, 2008 Field 3 | ||||
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12:00 pm | East Longmeadow | at VSA 2 | |
| Saturday, January 03, 2009 Field 3 | ||||
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9:00 am | Spfld. Utd. | at East Longmeadow | |
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10:00 am | VSA 1 | at VSA 2 | |
| Sunday, January 04, 2009 Field 3 | ||||
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2:00 pm | Spfld. Utd. | at Gold Star Soccer | |
| Saturday, January 10, 2009 Field 3 | ||||
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9:00 am | VSA 2 | at VSA 1 | |
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10:00 am | East Longmeadow | at Gold Star Soccer | |
| Sunday, January 11, 2009 Field 3 | ||||
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2:00 pm | East Longmeadow | at VSA 1 | |
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3:00 pm | Gold Star Soccer | at VSA 2 | |
| Saturday, January 17, 2009 Field 3 | ||||
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9:00 am | VSA 1 | at East Longmeadow | |
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10:00 am | VSA 2 | at Spfld. Utd. | |
| Sunday, January 18, 2009 Field 3 | ||||
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3:00 pm | VSA 1 | at Spfld. Utd. | |
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4:00 pm | VSA 2 | at Gold Star Soccer | |
| Friday, January 23, 2009 Field 3 | ||||
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8:00 pm | East Longmeadow | at Spfld. Utd. | |
| Saturday, January 24, 2009 Field 3 | ||||
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9:00 am | Gold Star Soccer | at Spfld. Utd. | |
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10:00 am | VSA 2 | at East Longmeadow | |
| Saturday, January 31, 2009 Field 3 | ||||
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9:00 am | VSA 1 | at Gold Star Soccer | |
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10:00 am | Spfld. Utd. | at VSA 2 | |