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All-Time NAIA $5,000 Sears Directors' Cup Winners
| Name | School | Year | Activity or Sport |
| Allison, Stephanie | Wayland Baptist University | 1996-97 | Sports Information Assistant |
| Amborn, Jennifer | MidAmerica Nazarene University | 1997-98 | Athletics Trainer |
| Baker, Frederick | Transylvania University | 1996-97 | Team Manager |
| Balcar, Petr | Simon Fraser University | 1998-99 | Athletics Trainer |
| Boy, Nichole | Friends University | 1995-96 | Assistant Coach |
| Burns, Adam | John Brown University | 2000-01 | Facilities Staff |
| Clement, Janalyn | William Jewell College | 1998-99 | Cheerleader |
| Clouser, Jason | College of the Ozarks | 2000-01 | Cheerleader |
| Collier, Crystal | Eastern Oregon University | 1999-2000 | Athletics Trainer |
| Davis, Brian | Transylvania University | 1995-96 | Team Manager |
| DiStefano, Jason | Pacific Lutheran University | 1995-96 | Assistant Coach |
| Foster, April | Wayland Baptist University | 1999-2000 | Athletics Trainer |
| Graham, Johan | Transylvania University | 1999-2000 | Cheerleader |
| Grahame, Sheri | Simon Fraser University | 1997-98 | Athletics Trainer |
| Han, James | Texas Lutheran University | 1997-98 | Athletics Trainer |
| Handlos, Janelle | Western Montana College | 1999-2000 | Athletics Trainer |
| Jurgens, Melonie | Hastings College | 1996-97 | Cheerleader |
| Lynch, Michael | Baker University | 1997-98 | Band Member |
| McKee, Barry | Hardin-Simmons University | 1995-96 | Athletic Athletics Trainer |
| McLain, Sara | St. Edward's University | 1997-98 | Team Manager |
| Phillips, Julie | Oklahoma Baptist University | 1998-99 | Cheerleader |
| Poole, Colleen | Simon Fraser University | 1999-2000 | Athletics Trainer |
| Rehder, Lisa | Lewis-Clark State College | 1998-99 | Assistant to Director of Athletics |
| Ring, Todd | Simon Fraser University | 1996-97 | Team Manager |
| Rodwell, Jenni | Albertson College | 2000-01 | Sports Information Assistant |
| Rupp, Keith | College of Mount St. Joseph | 1996-97 | Athletics Trainer |
| Ryan, Mary | Saint Ambrose University | 2000-01 | Athletics Trainer |
| Seeds (Tolman), Tanya | Black Hills State University | 1998-99 | Athletics Trainer |
| Villiers, Jim | Ambassador University | 1995-96 | Assistant Coach |
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