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Chesapeake Bowl History
| Year | Winning Team | Head Coach | Losing Team | Head Coach | Location | |||
| 2010 | South | 30 | BIff Poggi - Gilman (MD) | North | 27 | Terry Smith - Gateway (PA) | Towson University | |
| 2011 | North | 28 | Dan Alego - Cardinal O'Hara (PA) | South | 17 | Stan Sexton - Phoebus (VA) | South River HS | |
| 2012 | North | 38 | Jeff Weachter - Bishop McDevitt (PA) | South | 13 | Lawrence Smith - Dunbar (MD) | PG Sports & Learning |
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