| Year | Champion | Participants |
| 1965 | Southwood | Southwood, Baptist, Albemarle |
| 1966 | Chowan | Chowan, Brandywine, Campbell |
| 1967 | NA | Sand Hill, Albemarle, Cambell |
| 1968 | Mount Olive | Chesapeake, Sand Hill, Chowan |
| 1969 | Louisburg | Davidson, East Carolina (JV), Louisburg |
| 1970 | Louisburg | East Tennessee State (JV), UNC-Charlotte (JV), Louisburg |
| 1971 | Louisburg | East Carolina (JV), UNC-Charlotte (JV), Louisburg |
| 1972 | UNC-Charlotte | East Carolina (JV), UNC-Charlotte (JV), Louisburg |
| 1973 | Belmont | East Carolina (JV), Belmont, Louisburg |
| 1974 | Louisburg | East Carolina (JV), Belmont, Louisburg |
| 1975 | Louisburg | Southeastern, Louisburg, Frederick Military Academy |
| 1976 |
Frederick Military Academy |
Louisburg, Lenoir CC, Frederick Military Academy |
| 1978 | NA | Lenoir CC, USC-Lancaster, Surry CC |
| 1979 | Louisburg | USC-Lancaster, Louisburg, North Carolina (JV) |
| 1980 | Lenoir CC | Lenoir CC, Louisburg, USC-Lancaster |
| 1981 | Louisburg | Louisburg, USC-Lancaster, Craven CC |
| 1982 | Lenoir CC | Lenoir CC, Pembroke State (JV), Coastal Carolina (JV) |
| 1983 | Lenoir CC | Lenoir CC, Craven CC, Burrell Christian College of Rutledge |
| 1984 | Mount Olive | Anderson, Lenoir CC, Bland CC |
| 1985 | N.C. Wesleyan | Warren Wilson, Newport News Apprentice, N.C. Wesleyan |
| 1986 | Mount Olive | Mars Hill, Coker College, Newport News Apprentice |
| 1987 | Mount Olive | Coker College, N.C. Wesleyan, Newport News Apprentice |
| 1988 | Atlantic Christian | Christendom, Atlantic Christian, St. Andrews |
| 1989 | Elon | St. Andrews, Newport News Apprentice, Elon |
| 1990 | Mount Olive | Barber-Scotia, Virginia Intermont, Barton |
| 1991 | Barber-Scotia | Barber-Scotia, Newport News Apprentice, Barton |
| 1992 | Mount Olive | Gardner-Webb, Savannah State, Barton |
| 1993 | Mount Olive | Barton, Newport News Apprentice, St. Thomas (Fla.) |
| 1994 | Mount Olive | Morris College, Embry-Riddle, Barton |
| 1995 | Mount Olive | Lenoir-Rhyne, District of Columbia, Concordia |
| 1996 | District of Columbia | District of Columbia, North Florida, Emmanuel |
| 1997 | Mount Olive | Wingate, Barton, North Greenville |
| 1998 | Mount Olive | Tampa, Barton, Nova Southeastern |
| 1999 | USC-Aiken | Coker, USC-Aiken, Felician |
| 2000 | Mount Olive | Bluefield, UNC-Pembroke, Newberry |
| 2001 | Mount Olive | Mars Hill, Francis Marion, Emmanuel |
| 2002 | Mount Olive | Coker, Charleston, Davis and Elkins |
| 2003 | Mount Olive | Elizabeth City State, Longwood, Tampa |
| 2004 | Mount Olive | Bluefield State, Lees-McRae, Newberry |
| 2005 | Mount Olive | Chowan, Lees-McRae, UNC Pembroke |
| 2006 | Mount Olive | Chowan, Coker, Ohio Valley |
| 2007 | Mount Olive/King* | King, West Virginia State, Wingate |
| 2008 | USC-Aiken | Barton, Lenoir-Rhyne, USC-Aiken |
| 2009 | Mount Olive | Barton, Mars Hill, Virginia Union |
| 2010 | Mount Olive | Chowan, Mars Hill, North Georgia |
| 2011 | Mount Olive/Barton | Barton, Brevard, Virginia State |
| 2012 | Lenoir-Rhyne | Fayetteville State, Lenoir-Rhyne, West Virginia State |
| 2013 | Virginia State | Barton, Saint Augustine's, Virginia State |
| 2014 | Mount Olive | Barton, Bluefield State, Virginia State |
| 2015 | UNC Pembroke | Virginia State, Barton, UNC Pembroke |
| 2016 | Barton | Barton, Georgian Court, Saint Augustine's |
| 2017 | Mount Olive | Barton, Saint Augustine's, Virginia Union |
*The Pickle Classic switched from a tournament format to a round-robin format in 2007. Team with best record listed as Pickle Classic champion each year since 2007.