Named in honor of ski racing legend Jack Tobin, this award is given to an Eastern Masters racer (New England, New York or Mid-Atlantic divisions) for “outstanding contribution to Eastern Masters Ski Racing”.
| Jack Tobin Award | |||||
| 1990 | Al Sise | 2000 | Marshall & Joan Skiff | 2010 | George Caner |
| 1991 | Faith Middleton | 2001 | David “Duffy” Dodge | 2011 | George Merrill |
| 1992 | Gary Colwell | 2002 | Bob & Pam Fisher | 2012 | Pepe Neubauer |
| 1993 | Jane Hough | 2003 | Dick Prentice | 2013 | Pete Donaghy |
| 1994 | Bob & Cheryl Risberger | 2004 | Bob McGrath | 2014 | Horst Locher |
| 1995 | Alan Beck | 2005 | Bromley Outing Club | 2015 | David Strang |
| 1996 | Fraser Noble | 2006 | Paul Rich | 2016 | Peter Cornish & Okemo Mt. Race Crew |
| 1997 | Cynthia Lathrop | 2007 | Ski Club Hochgebirge | 2017 | |
| 1998 | Dick Comey | 2008 | George Anderson | 2018 | Anne Nordhoy |
| 1999 | Jim & Jane Cook | 2009 | Bill McCollom | 2019 |
Hubert Schriebel |