Records as of 05/28/2008 for the top 40
* No longer a Head Coach or not coaching
| Head Coach | Wins | Losses | Years as Head Coach | School(s) |
| Rev. Father Robert Kinney | 411 | 168 | 34 | Salesianum School |
| Larry Wheeler | 397 | 154 | 29 | Claymont H.S. (14) Brandywine H.S. (12) DE Military (3) |
| Bob Colburn | 394 | 382 |
48 | St. Andrew's School |
| Mel Gardner | 359 | 181 | 28 | William Penn H.S. |
| John Newman | 322 | 150 | 24 | Caesar Rodney H.S. |
| Paul Niggebrugge | 291 | 145 | 22 | Caravel Academy |
| Richard Green * | 257 | 111 | 19 | Middletown H.S. |
| Tom Lemon | 255 | 103 | 17 | St. Mark's H.S. (16) Sanford School (2) |
| Dick Russo * | 243 | 109 | 20 | John Dickinson H.S. |
| Fran Fulghum * | 235 | 110 | 21 | Newark H.S. |
| Harry Davies * | 232 | 128 | 17 | Newark H.S. (9) Wilmington (8) |
| Tom Beddow | 235 | 186 | 22 | St. Elizabeth's H.S. |
| Vince Filliben * | 215 | 31 | Archmere Academy | |
| Jim Thompson * | 209 | 158 | 27 | Concord H.S. |
| Dennis Walker * | 204 | 86 | 14 | Salesianum School |
| Tom Pegelow | 215 | 89 | 15 | Seaford H.S. (13) Sussex Tech H.S. (2) |
| Frank Aiello * | 187 | 97 | 16 | St. Elizabeth's H.S. |
| Rob Limmina * | 183 | 144 | 18 | Mt. Pleasant H.S. |
| Gus Highfield * | 170 | 165 | 20 | Thomas McKean H.S. |
| Matt Smith | 177 | 38 | 10 | St. Mark's H.S. |
| John Nelson | 170 | 63 | 11 | John Dickinson H.S. |
| David Hearn | 151 | 158 | 17 | Delmar H.S. |
| Curt Bedford * | 134 | 67 | 10 | Newark H.S. |
| Jim Hudson * | 129 | 74 | 11 | Sussex Central H.S. |
| Len Chasnov * | 121 | 108 | 14 | Seaford H.S. Woodbridge H.S. |
| Bob Turnberger * | 120 | 50 | 17 | Christiana H.S. |
| Jerry Mears | 118 | 107 | 11 | Laurel H.S. |
| Glenn Gabrelcik | 115 | 95 | 13 | Dover H.S. |
| Chuck Clausius | 110 | 104 | 10 | Pennsville H.S (3) Brandywine H.S. (6) Archmere Academy (1) |
| Vern Higgins * | 97 | 143 | 13 | Delcastle Technicall |
| Ron Dickerson * | 96 | 17 | 07 | Seaford H.S. |
| Mike King* | 94 | 71 | 09 | Indian River H.S. |
| Don Kurcon * | 94 | 76 | 10 | Tatnall School |
| Billy Cannon | 93 | 60 | 08 | Tower Hill School |
| Bill Cole * | 90 | 70 | 13 | William Penn H.S. |
| Scott Smith | 89 | 75 | 08 | Middletown H.S. |
| Ray Pusey | 88 | 63 | 08 | Red Lion Christian Acad |
| Doug Nowell | 88 | 75 | 08 | Delcastle Technicall (2) A.I. Dupont H.S.(3) Salesianum School (3) |
| John Nichols | 88 | 107 | 11 | Woodbridge H.S. (6) Milford H.S. (5) |
| George Eilers | 87 | 52 | 07 | Polytech H.S. |
Please note that there may be errors in these and if so, please email Bob Colburn. Also,
there are several coaches for whom no records were found. Please email Bob if you know the
records of Bill Falasco, Steve Lenox, Bob Tattersall, Jim Tosi, Randy Nowell, Willie Miranda,
Dick Durbano, and Woody Long.