Bob Hollendonner was a 20 year member who passed away in April of 1988. To honor Bob, the Club officers and directors voted in 1989 to give a trophy-plaque to the member who showed the most improvement in his or her skiing ability.
| 1988-89 | Art Lavinthal | |
| 1989-90 | Pete Burns | |
| 1990-91 | Paul Tremblay | |
| 1991-92 | Cindy Winters | |
| 1992-93 | Ken Mastalesz | |
| 1993-94 | Tammy Duffy | |
| 1994-95 | Caroline Germond | |
| 1995-96 | Karen Wyszynski & Don Walker | |
| 1996-97 | Joan Sabatini | |
| 1997-98 | Ken Boyle | |
| 1998-99 | Cathy Stone | |
| 1999-00 | Cheryle Fasolino | |
| 2000-01 | Ken Scott | |
| 2001-02 | Jim Huckfeldt | |
| 2002-03 | Marcy Cohen | |
| 2003-04 | Marlene O'Neill | |
| 2004-05 | Sue Golden | |
| 2005-2006 | Jennifer Toto | |
| 2006-2007 |
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