| Year | Name | Company | Chapter |
| 1995 | Paula Tomchak | Unique Images by Paula / WBN Founding Member | Robinson Township |
| 1996 | Rebecca Leonard | Leonard’s Antique Mega Mall | Beaver |
| 1997 | Bonnie DiCarlo | Bonnie V. Dicarlo, CFP | East |
| 1998 | |||
| 1999 | S. C. (Sheena) Cardello | S. C. Cardello Co. & Kids Ride Away Transportation Co. | Downtown |
| 2000 | Annette Merlino, DMD | Annette Merlino DMD | Murraysville |
| 2001 | Carol Venzin | Fantastic Sams | North Versailles |
| 2002 | Renee DeMichiei-Farrow | Decorating Details / NAWBO President | East |
| 2003 | Donna Meshanko | Mary Kay Cosmetics | East |
| 2004 | Angela Rose-O’Brien | Inspiring Times | Laurel Highlands |
| 2005 | Susan Miller | Pittsburgh Candle Co. | Points North |
| 2006 | Linda Ruckert | Linda’s Imprinted Products | East |
| 2007 | Patty Kreamer | Kreamer Connect, Inc. | East |
