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| March 5, 2009 | 4:00 PM | Landstown | Poquoson | Scrimmage | | March 13, 2009 | 4:00PM | Landstown | First Colonial | L 8-6 | | March 17, 2009 | 4:00 PM | Salem | Landstown | W 11-3 | | March 20, 2009 | 4:00 PM | Cox | Landstown | L 15-1 | | March 24, 2009 | 4:00 PM | Landstown | Bayside | W 11-3 | | March 27, 2009 | 4:00 PM | Green Run | Landstown | W 12-3 | | March 31, 2009 | 4:00 PM | Landstown | Tallwood | L 1-0 | | April 3, 2009 | Bye | Bye | Bye | Bye | | April 7, 2009 | 4:00 PM | Landstown | Ocean Lakes | L 9-6 | | April 8, 2009 | 4:00PM | Kempsville | Landstown | W 6-4 | | April 11, 2009 | 1:00AM | Landstown | Lakeland | W 8-7 | | April 11, 2009 | 4:00PM | Landstown | Nansemond River | L 9-3 | | April 13, 2009 | 11:00AM | Landstown | Hickory | L 7-3 | | April 13, 2009 | 5:00PM | Landstown | Indian River | L 8-4 | | April 21, 2009 | 4:00PM | Landstown | Kellam | L 9-4 | | April 24, 2009 | 4:00PM | Princess Anne | Landstown | W 7-4 | | April 28, 2009 | 4:00PM | Tallwood | Landstown | W 7-3 | | May 1, 2009 | 4:00PM | Landstown | Green Run | W 4-3 | | May 5, 2009 | 4:00PM | Bayside | Landstown | W 9-5 | | May 8, 2009 | 4:00PM | Landstown | Cox | L 8-3 | | May 11, 2009 | 4:00PM | Landstown | Salem | L 11-5 | | May 13, 2009 | 4:00PM | First Colonial | Landstown | L 7-6 | | May 16, 2009 | 10:00 AM | 1 Seed | 8 Seed | Cox 4-3 | | May 16, 2009 | 1:00 PM | 4 Seed | 5 Seed | PA 3-0 | | May 16, 2009 | 4:00 PM | 2 Seed | 7 Seed | Kempsville 4-3 | | May 16, 2009 | 7:00 PM | 3 Seed | 6 Seed | FC 5-3 | | May 19, 2009 | 4:00 PM | 4 vs. 5 winner | 8 vs. 1 winner | Cox | | May 19, 2009 | 7:00 PM | 3 vs. 6 winner | 2 vs. 7 winner | FC 5-4 | | May 21, 2009 | 7:00 PM | District Tournament Championship | District Tournament Championship | FC 14-7 |
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