| The Olin Simpson Award is the highest honor a Region can bestow upon a member for outstanding service. The award is only given out when the nomination committee has a candidate worthy of the honor, thus the award may not be given out every year. | |
| 1981 | Larry Wacker, C4 |
| 1983 | William Huot, C172 |
| 1984 | Frank Trcka |
| 1986 | Marvin DeVries, C75 |
| 1988 | Ken Koch, C222 |
| 1990 | Charles Eckart, C4 |
| 1991 | Vern Stumpenhorst, C194 |
| 1992 | Lew Fruchtl, C194 |
| 1993 | Glen I Schrock, C186 |
| 1994 | Donald Williams, C75 |
| 1995 | Thomas L. Linn, C4 |
| 1996 | Michael Gallagher, C75 |
| 1997 | Arnie Pfannenstein, C194 |
| 1998 | Thomas Vanderloop, C335 |
| 1999 | Joe Kraft, C045 |
| 2000 | Ron Vander Weerd, C186 |
| 2001 | Carolyn J. Walker, C238 |