Named in honor of Al Sise, the father of alpine masters ski racing and a member of both the Vermont Ski Museum Hall of Fame and the National Ski Hall of Fame. The Sise Cup is the most prestigious award within the New England Masters and is bestowed to the top man and women points holders at the end of each race season.
| Sise Cup Champions | |||||
| Year | Men | Women | Year | Men | Women |
| 1971 | Brooks Dodge | 2001 | Will Withington | Caroline Beckedorff | |
| 1972 | Rodger Buchika | 2002 | Chris Johnson | Jessie McAleer | |
| 1973 | Rodger Buchika | 2003 | Bob Hill | Jessie McAleer | |
| 1974 | Brooks Dodge | 2004 | Matt Aeschliman | Jessie McAleer | |
| 1975 | Rodger Buchika | 2005 | Bob Hill | Caroline Beckedorff | |
| 1976 | Rodger Buchika | 2006 | David Wolff | Jessie McAleer | |
| 1977 | Rodger Buchika | Debbie McLane | 2007 | Mark George | Caroline Beckedorff |
| 1978 | Rodger Buchika | Debbie McLane | 2008 | Randy Detrick | Caroline Beckedorff |
| 1979 | Jeff Jacobs | Debbie McLane | 2009 | Ben Green | Jessie McAleer |
| 1980 | Peter Cater | Debbie Carter | 2010 | Ben Green | Jessie McAleer |
| 1981 | Peter Cater | Susan MacNeil | 2011 | Mark George | Jessie McAleer |
| 1982 | Peter Cater | Susan Fisher | 2012 | Ben Green | Katie George Green |
| 1983 | John Macomber | Debbie Carter | 2013 | Ben Green | Katie George Green |
| 1984 | John Macomber | Debbie Carter | 2014 | Ben Green | Lisa Marien |
| 1985 | Bob Rose | Debbie Carter | 2015 | Matthew Dodge | Alex Mitchell |
| 1986 | Bob Rose | Susan Fisher | 2016 | Kevin O’Brien | Jackie Levy |
| 1987 | Rich Wright / David Dodge | Joan Crane Barthold | 2017 | Kevin O’Brien | Taylor Knortz |
| 1988 | Bob Hill | Joan Crane Barthold / Kathy-Rae Presby | 2018 | Matthew Dodge | Jackie Levy |
| 1989 | Rich Wright | Joan Crane Barthold | 2019 | Matthew Dodge | Alex Mitchell |
| 1990 | Wayne Wright | Kathy-Rae Presby | 2020 | Matthew Dodge | Alex Mitchell |
| 1991 | Bob Hill | Lisa Feinberg Densmore | 2021 | Matthew Dodge | Becka Padgett |
| 1992 | Bob Hill | Joan Crane Barthold | 2022 | Matthew Dodge | Kerry Finch |
| 1993 | William McGrath | Lisa Feinberg Densmore | 2023 | Matthew Dodge | Becka Padgett |
| 1994 | William McGrath | Lisa Feinberg Densmore | |||
| 1995 | Tyler Palmer | Kim Wolff | |||
| 1996 | William McGrath | Lisa Feinberg Densmore | |||
| 1997 | William McGrath | Brooks Axelson | |||
| 1998 | Chris Johnson | Brooks Axelson | |||
| 1999 | Chris Johnson | Lisa Feinberg Densmore | |||
| 2000 | Chris Johnson | Melissa Patterson |