The Calcutta Fishing Derby is sponsored by the Woods Hole Business Association and takes place the entire month of September with daily prizes given out for biggest catch of Bluefish and Bass. Grand prizes given out on the last day of the derby.
| Past Winners |
| Year | Men's Bass | Men's Bluefish | Women's Bass | Women's Bluefish | Under 12 |
| 2009 |
Phil Stanton 38.25 lb. |
Gary Engblom - 15.8 lb. |
Kelly Livingston - 23.5 lb. |
Katrin Tessier - 11.1 lb. |
Linny Delinks - 11.4 lb. Blue Aidan Downey - 9.55 lb. Bass |
| 2008 |
Nat Chakley - 49.6 lbs. |
Nat Chakley - 13.35 lbs. |
Rachel Delori - 15.45 lb. |
Lisa Danburg - 12.3 lb. |
Ariella Baxbaum Grice 3.45 lb. Bluefish |
| 2007 |
Miles Ochs - 42.9 lbs. |
Ed Dupuis - 13.1 lbs. |
Laurie Raymond - 9.05 lb. |
Lindsey Duquay - 21.3 lb. |
Linny Delinks - 1 lb. |
| 2006 |
Erik Gura - 38.3 lbs. |
Gary Engblom - 14.9 lbs. |
Laurie Raymond - 9.8 lb. |
Laurie Raymond - 11.95 lb. |
Lindsay Delinks (8 yrs. old) 1.1 lb. Bluefish |
| 2005 |
Nat Chalkley - 36.7 lbs. |
Phil Stanton - 12.9 lbs. |
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| 2004 |
Andrew Grant - 40.3 lbs. |
Phil Stanton - 13.8 lbs. |
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