Rambler New Hampshire Schooner [Moore Maley]
 Randolph Connecticut Sloop [Fosdick Peck Fosdick Peck]
 Ranger Connecticut Brig [Lathrop]
 Ranger Massachusetts Schooner [Roberts]
 Rattlesnake Connecticut Boat [Burnham]
 Rattlesnake Connecticut Boat [Jones]
 Rattlesnake Massachusetts Schooner [Johnson]
 Rattlesnake Massachusetts Ship [Clark]
 Rattlesnake Massachusetts Sloop [Stone]
 Rattlesnake Pennsylvania Schooner [Ball Craig Mansfield Treen Snell Stephens]
 Rattlesnake Pennsylvania Schooner [McCullough]
 Rattlesnake Virginia Ship [Cannon]
 Rebecca and Sally Maryland Schooner [Russell]
 Reprisal Massachusetts Brigantine [Wheelwright]
 Reprisal Massachusetts Sloop [Carver]
 Retaliation Massachusetts Brigantine [Giles]
 Retaliation Rhode Island Sloop [Jones Tillinghast Westcott]
 Retrieve Massachusetts Sloop [Stone]
 Revenge Connecticut Sloop [Conkling Post Parker]
 Revenge Massachusetts Sloop [White Warren Dean]
 Revenge New York [unknown] [Griffin]
 Revenge Rhode Island Sloop [Dunn Sheffield]
 Rhodes Massachusetts Ship [Buffinton]
 Rising States Massachusetts Brig [Thompson]
 Rover Massachusetts Sloop [Forrester Boden Mitchell]
 Rover New Hampshire Schooner [Smith Bradstreet]
 Rover Rhode Island Sloop [Horne]
 Roxene New Hampshire Brigantine [Kitson]
 Royal Louis New Hampshire Ship [Nichols]
 Run Fast Massachusetts Schooner [Somes]
 Ruth New Hampshire Brigantine [Jewett]
 Rutledge Pennsylvania Brig [Smith]
 Rutledge South Carolina Sloop [Milligan Porter]