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 | 1991 | Faith Middleton | 1992 | Gary Colwell |
| 1993 | Jane Hough | 1994 | Bob & Cheryl Risberger | 1995 | Alan Beck |
| 1996 | Fraser Noble | 1997 | Cynthia Lathrop | 1998 | Dick Comey |
| 1999 | Jim & Jane Cook | 2000 | Marshall & Joan Skiff | 2001 | David "Duffy" Dodge |
| 2002 | Bob & Pam Fisher | 2003 | Dick Prentice | 2004 | Bob McGrath |
| 2005 | Bromley Outing Club | 2006 | Paul Rich | 2007 | Ski Club Hochgebirge |
| 2008 | George Anderson | 2009 | Bill McCollom | 2010 | George Caner |
| 2011 | George Merrill | 2012 | Pepe Neubauer | 2013 | Peter Donaghy |
| 2014 | Horst Locher | 2015 | David Strang | 2016 | Peter Cornish & Okemo Mt Race Crew |
| 2017 | 2018 | Anne Nordhoy | 2019 | Hubert Shcriebel |