Szary Kielich to święty Graal Kanadyjska Liga Piłkarska dzięki temu mistrzowie West Division zmierzą się z mistrzami East Division. Zdobywca Pucharu Grey po raz pierwszy został koronowany w 1909 roku przed kilkoma tysiącami ludzi, dzięki czemu jest teraz jednym z obowiązkowych wydarzeń sportowych w kanadyjskim kalendarzu sportowym.
| Data | Zwycięska drużyna | Przegrana drużyna | Wynik | Miejsce wydarzenia | Miasto | |
| 1909 | University of Toronto Varsity Blues | Toronto Parkdale Canoe Club | 26–6 | Rosedale Field | Toronto | 3,807 |
| 1910 | University of Toronto Varsity Blues | Hamilton Tigers | 16–7 | Podstawy AAA | Hamilton | 12,000 |
| 1911 | University of Toronto Varsity Blues | Toronto Argonauts | 14–7 | Stadion uniwersytecki | Toronto | 13,687 |
| 1912 | Hamilton Alerts | Toronto Argonauts | 11–4 | Podstawy AAA | Hamilton | 5,337 |
| 1913 | Hamilton Tigers | Toronto Parkdale Canoe Club | 44–2 | Podstawy AAA | Hamilton | 2,100 |
| 1914 | Toronto Argonauts | University of Toronto Varsity Blues | 14–2 | Stadion uniwersytecki | Toronto | 10,500 |
| 1915 | Hamilton Tigers | Toronto Rowing Association | 13–7 | Stadion uniwersytecki | Toronto | 2,808 |
| 1916-1919 | Brak gier | — | — | — | — | — |
| 1920 | University of Toronto Varsity Blues | Toronto Argonauts | 16–3 | Stadion uniwersytecki | Toronto | 10,088 |
| 1921 | Toronto Argonauts | Eskimosi z Edmonton | 23–0 | Stadion uniwersytecki | Toronto | 9,558 |
| 1922 | Queen’s University | Edmonton Elks | 13–1 | Richardson Stadium | Kingston | 4,700 |
| 1923 | Queen’s University | Queen Rugby Club | 54–0 | Stadion uniwersytecki | Toronto | 8,629 |
| 1924 | Queen’s University | Toronto Balmy Beach | 11–2 | Stadion uniwersytecki | Toronto | 5,978 |
| 1925 | Senatorowie z Ottawy | Winnipeg Tammany Tigers | 24–1 | Lansdowne Park | Ottawa | 6,900 |
| 1926 | Senatorowie z Ottawy | Toronto Varsity Blues | 10–7 | Stadion uniwersytecki | Toronto | 8,276 |
| 1927 | Toronto Balmy Beach | Hamilton Tigers | 9–6 | Stadion uniwersytecki | Toronto | 13,676 |
| 1928 | Hamilton Tigers | Regina Roughriders | 30–0 | Podstawy AAA | Hamilton | 4,767 |
| 1929 | Hamilton Tigers | Regina Roughriders | 14–3 | Podstawy AAA | Hamilton | 1,906 |
| 1930 | Toronto Balmy Beach | Regina Roughriders | 11–6 | Stadion uniwersytecki | Toronto | 3,914 |
| 1931 | Montreal AAA Winged Wheelers | Regina Roughriders | 22–0 | Stadion Molsona | Montreal | 5,112 |
| 1932 | Hamilton Tigers | Regina Roughriders | 25–6 | Podstawy AAA | Hamilton | 4,806 |
| 1933 | Toronto Argonauts | Sarnia Imperials | 4–3 | Athletic Park | Sarnia | 2,751 |
| 1934 | Sarnia Imperials | Regina Roughriders | 20–12 | Stadion uniwersytecki | Toronto | 8,900 |
| 1935 | Winnipeg „Pegs | Hamilton Tigers | 18–12 | Podstawy AAA | Hamilton | 6,405 |
| 1936 | Sarnia Imperials | Ottawa Rough Riders | 26–20 | Stadion uniwersytecki | Toronto | 5,883 |
| 1937 | Toronto Argonauts | Niebieskie bombowce Winnipeg | 4–3 | Stadion uniwersytecki | Toronto | 11,522 |
| 1938 | Toronto Argonauts | Niebieskie bombowce Winnipeg | 30–7 | Stadion uniwersytecki | Toronto | 18,778 |
| 1939 | Niebieskie bombowce Winnipeg | Ottawa Rough Riders | 8–7 | Lansdowne Park | Ottawa | 11,737 |
| 1940 | Ottawa Rough Riders | Toronto Balmy Beach | 8–2 | Stadion uniwersytecki | Toronto | 4,998 |
| Ottawa Rough Riders | 12–5 | Lansdowne Park | Toronto Balmy Beach | Ottawa | 1,700 | |
| 1941 | Niebieskie bombowce Winnipeg | Ottawa Rough Riders | 18-16 | Stadion uniwersytecki | Toronto | 19,065 |
| 1942 | Toronto RCAF Hurricanes | Bombowce Winnipeg RCAF | 8–5 | Stadion uniwersytecki | Toronto | 12,455 |
| 1943 | Hamilton Latające Wildcats | Bombowce Winnipeg RCAF | 23–14 | Stadion uniwersytecki | Toronto | 16,423 |
| 1944 | Marynarka St. Hyacinthe-Donnacona | Hamilton Latające Wildcats | 7–6 | Stadion Obywatelski | Hamilton | 3,871 |
| 1945 | Toronto Argonauts | Niebieskie bombowce Winnipeg | 35–0 | Stadion uniwersytecki | Toronto | 18,660 |
| 1946 | Toronto Argonauts | Niebieskie bombowce Winnipeg | 28–6 | Stadion uniwersytecki | Toronto | 18,960 |
| 1947 | Toronto Argonauts | Niebieskie bombowce Winnipeg | 10–9 | Stadion uniwersytecki | Toronto | 18,885 |
| 1948 | Calgary Stampeders | Ottawa Rough Riders | 12–7 | Stadion uniwersytecki | Toronto | 20,013 |
| 1949 | Montreal Alouettes | Calgary Stampeders | 28-15 | Stadion uniwersytecki | Toronto | 20,087 |
| 1950 | Toronto Argonauts | Niebieskie bombowce Winnipeg | 13–0 | Stadion uniwersytecki | Toronto | 27,101 |
| 1951 | Ottawa Rough Riders | Saskatchewan Roughriders | 21–14 | Stadion uniwersytecki | Toronto | 27,341 |
| 1952 | Toronto Argonauts | Eskimosi z Edmonton | 21–11 | Stadion uniwersytecki | Toronto | 27,391 |
| 1953 | Hamilton Tiger-Cats | Niebieskie bombowce Winnipeg | 12–6 | Stadion uniwersytecki | Toronto | 27,313 |
| 1954 | Eskimosi z Edmonton | Montreal Alouettes | 26–25 | Stadion uniwersytecki | Toronto | 27,328 |
| 1955 | Eskimosi z Edmonton | Montreal Alouettes | 34–19 | Empire Stadium | Vancouver | 27,301 |
| 1956 | Eskimosi z Edmonton | Montreal Alouettes | 50–27 | Stadion uniwersytecki | Toronto | 39,417 |
| 1957 | Hamilton Tiger-Cats | Niebieskie bombowce Winnipeg | 32–7 | Stadion uniwersytecki | Toronto | 27,425 |
| 1958 | Niebieskie bombowce Winnipeg | Hamilton Tiger-Cats | 35–28 | Empire Stadium | Vancouver | 27,391 |
| 1959 | Niebieskie bombowce Winnipeg | Hamilton Tiger-Cats | 21–7 | Stadion CNE | Toronto | 34,426 |
| 1960 | Ottawa Rough Riders | Eskimosi z Edmonton | 16–6 | Empire Stadium | Vancouver | 33,133 |
| 1961 | Niebieskie bombowce Winnipeg | Hamilton Tiger-Cats | 21–14 | Stadion CNE | Toronto | 36,592 |
| 1962 | Niebieskie bombowce Winnipeg | Hamilton Tiger-Cats | 28–27 | Stadion CNE | Toronto | 32,655 |
| 1963 | Hamilton Tiger-Cats | BC Lions | 21–10 | Empire Stadium | Vancouver | 36,465 |
| 1964 | BC Lions | Hamilton Tiger-Cats | 34–24 | Stadion CNE | Toronto | 32,655 |
| 1965 | Hamilton Tiger-Cats | Niebieskie bombowce Winnipeg | 22-16 | Stadion CNE | Toronto | 32,655 |
| 1966 | Saskatchewan Roughriders | Ottawa Rough Riders | 29-14 | Empire Stadium | Vancouver | 32,344 |
| 1967 | Hamilton Tiger-Cats | Saskatchewan Roughriders | 24–1 | Lansdowne Park | Ottawa | 31,407 |
| 1968 | Ottawa Rough Riders | Calgary Stampeders | 24–21 | Stadion CNE | Toronto | 33,185 |
| 1969 | Ottawa Rough Riders | Saskatchewan Roughriders | 29–11 | Autostade | Montreal | 33,172 |
| 1970 | Montreal Alouettes | Calgary Stampeders | 23–10 | Stadion CNE | Toronto | 32,669 |
| 1971 | Calgary Stampeders | Toronto Argonauts | 14–11 | Empire Stadium | Vancouver | 34,584 |
| 1972 | Hamilton Tiger-Cats | Saskatchewan Roughriders | 13–10 | Stadion Ivor Wynne | Hamilton | 35,950 |
| 1973 | Ottawa Rough Riders | Eskimosi z Edmonton | 22–18 | Stadion CNE | Toronto | 36,475 |
| 1974 | Montreal Alouettes | Eskimosi z Edmonton | 20–7 | Empire Stadium | Vancouver | 34,450 |
| 1975 | Eskimosi z Edmonton | Montreal Alouettes | 9–8 | Stadion McMahon | Calgary | 32,454 |
| 1976 | Ottawa Rough Riders | Saskatchewan Roughriders | 23–20 | Stadion CNE | Toronto | 53,389 |
| 1977 | Montreal Alouettes | Eskimosi z Edmonton | 41–6 | stadion Olimpijski | Montreal | 68,205 |
| 1978 | Eskimosi z Edmonton | Montreal Alouettes | 20–13 | Stadion CNE | Toronto | 54,695 |
| 1979 | Eskimosi z Edmonton | Montreal Alouettes | 17–9 | stadion Olimpijski | Montreal | 65,113 |
| 1980 | Eskimosi z Edmonton | Hamilton Tiger-Cats | 48–10 | Stadion CNE | Toronto | 54,661 |
| 1981 | Eskimosi z Edmonton | Ottawa Rough Riders | 26–23 | stadion Olimpijski | Montreal | 52,478 |
| 1982 | Eskimosi z Edmonton | Toronto Argonauts | 32-16 | Stadion CNE | Toronto | 54,741 |
| 1983 | Toronto Argonauts | BC Lions | 18–17 | BC Place | Vancouver | 59,345 |
| 1984 | Niebieskie bombowce Winnipeg | Hamilton Tiger-Cats | 47-17 | Stadion Wspólnoty Narodów | Edmonton | 60,081 |
| 1985 | BC Lions | Hamilton Tiger-Cats | 37–24 | stadion Olimpijski | Montreal | 56,723 |
| 1986 | Hamilton Tiger-Cats | Eskimosi z Edmonton | 39-15 | BC Place | Vancouver | 59,579 |
| 1987 | Eskimosi z Edmonton | Toronto Argonauts | 38–36 | BC Place | Vancouver | 59,478 |
| 1988 | Niebieskie bombowce Winnipeg | BC Lions | 22–21 | Lansdowne Park | Ottawa | 50,604 |
| 1989 | Saskatchewan Roughriders | Hamilton Tiger-Cats | 43–40 | SkyDome | Toronto | 54,088 |
| 1990 | Niebieskie bombowce Winnipeg | Eskimosi z Edmonton | 50–11 | BC Place | Vancouver | 46,968 |
| 1991 | Toronto Argonauts | Calgary Stampeders | 36–21 | Stadion Winnipeg | Winnipeg | 51,985 |
| 1992 | Calgary Stampeders | Niebieskie bombowce Winnipeg | 24–10 | SkyDome | Toronto | 45,863 |
| 1993 | Eskimosi z Edmonton | Niebieskie bombowce Winnipeg | 33–23 | Stadion McMahon | Calgary | 50,035 |
| 1994 | BC Lions | Baltimore Football Club | 26–23 | BC Place | Vancouver | 55,097 |
| 1995 | Baltimore Stallions | Calgary Stampeders | 37–20 | Taylor Field | Regina | 52,564 |
| 1996 | Toronto Argonauts | Eskimosi z Edmonton | 43–37 | Stadion Ivor Wynne | Hamilton | 38,595 |
| 1997 | Toronto Argonauts | Saskatchewan Roughriders | 47–23 | Stadion Wspólnoty Narodów | Edmonton | 60,431 |
| 1998 | Calgary Stampeders | Hamilton Tiger-Cats | 26–24 | Stadion Winnipeg | Winnipeg | 34,157 |
| 1999 | Hamilton Tiger-Cats | Calgary Stampeders | 32–21 | BC Place | Vancouver | 45,118 |
| 2000 | BC Lions | Montreal Alouettes | 28–26 | Stadion McMahon | Calgary | 43,822 |
| 2001 | Calgary Stampeders | Niebieskie bombowce Winnipeg | 27–19 | stadion Olimpijski | Montreal | 65,255 |
| 2002 | Montreal Alouettes | Eskimosi z Edmonton | 25-16 | Stadion Wspólnoty Narodów | Edmonton | 62,531 |
| 2003 | Eskimosi z Edmonton | Montreal Alouettes | 34–22 | Taylor Field | Regina | 50,909 |
| 2004 | Toronto Argonauts | BC Lions | 27–19 | Stadion Frank Clair | Ottawa | 51,242 |
| 2005 | Eskimosi z Edmonton | Montreal Alouettes | 38–35 | BC Place | Vancouver | 59,157 |
| 2006 | BC Lions | Montreal Alouettes | 25–14 | Stadion Canad Inns | Winnipeg | 44,786 |
| 2007 | Saskatchewan Roughriders | Niebieskie bombowce Winnipeg | 23–19 | Rogers Center | Toronto | 52,230 |
| 2008 | Calgary Stampeders | Montreal Alouettes | 22–14 | stadion Olimpijski | Montreal | 66,308 |
| 2009 | Montreal Alouettes | Saskatchewan Roughriders | 28–27 | Stadion McMahon | Calgary | 46,020 |
| 2010 | Montreal Alouettes | Saskatchewan Roughriders | 21–18 | Stadion Wspólnoty Narodów | Edmonton | 63,317 |
| 2011 | BC Lions | Niebieskie bombowce Winnipeg | 34–23 | BC Place | Vancouver | 54,313 |
| 2012 | Toronto Argonauts | Calgary Stampeders | 35–22 | Rogers Center | Toronto | 53,208 |
| 2013 | Saskatchewan Roughriders | Hamilton Tiger-Cats | 45–23 | Stadion Mozaiki | Regina | 44,710 |
| 2014 | Calgary Stampeders | Hamilton Tiger-Cats | 20-16 | BC Place | Vancouver | 52,056 |
| 2015 | Eskimosi z Edmonton | Ottawa Redblacks | 26–20 | Pole Investors Group | Winnipeg | 36,634 |
| 2016 | Ottawa Redblacks | Calgary Stampeders | 39–33[RE] | BMO Field | Toronto | 33,421 |
| 2017 | Toronto Argonauts | Calgary Stampeders | 27–24 | Stadion TD Place | Ottawa | 36,154 |
| 2018 | Calgary Stampeders | Ottawa Redblacks | 27-16 | Stadion Wspólnoty Narodów | Edmonton | 55,819 |
| 2019 | Niebieskie bombowce Winnipeg | Hamilton Tiger-Cats | 33–12 | Stadion McMahon | Calgary | 35,440 |