2014 James M. Bennett
| 2014 James M. Bennett (3-7) |
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| Date | H/A | Opponent | PF | PA | W/L | League/Note |
| 9-5 | A | Easton | 20 | 48 | L | 0-1, BAY32 |
| 9-12 | H | Nandua (Va.) | 28 | 20 | W | – |
| 9-19 | H | Parkside | 14 | 33 | L | 0-2, BAY32 |
| 9-26 | A | Snow Hill | 48 | 20 | W | – |
| 10-2 | H | North Caroline | 25 | 42 | L | 0-3, BAY32 |
| 10-10 | A | Queen Anne’s | 13 | 47 | L | 0-4, BAY32 |
| 10-17 | H | Cambridge-S.D. | 20 | 49 | L | – |
| 10-25 | H | Stephen Decatur | 55 | 41 | W | 1-4, BAY32 |
| 10-31 | A | Kent Island | 0 | 48 | L | 1-5, BAY32 |
| 11-7 | H | Wicomico | 13 | 42 | L | 1-6, BAY32 |
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