Juvenile/Under-21 AAA Champions
| YEAR | A | B |
| 1912-13 | ST. MATTHEWS | |
| 1913-14 | AURA LEE | |
| 1914-15 | ST. SIMONS | |
| 1915-16 | ST. MARYS | |
| 1916-17 | CENTURY ROVERS | |
| 1917-18 | DE LA SALLE | |
| 1918-19 | WYCHWOOD | |
| 1919-20 | MELVRIS | |
| 1920-21 | MAITLANDS | |
| 1921-22 | THISTLES | |
| 1922-23 | ARGONAUTS | |
| 1923-24 | HEPBURNS | |
| 1924-25 | RIVERDALE | |
| 1925-26 | DANFORTHS | |
| 1926-27 | MAITLANDS | |
| 1927-28 | MOORE PARK | |
| 1928-29 | MOORE PARK | |
| 1929-30 | OKE AC | |
| 1930-31 | DE LA SALLE | |
| 1931-32 | MIC MACS | |
| 1932-33 | WOODBRIDGE | |
| 1933-34 | FOREST HILL | |
| 1934-35 | NORTH TORONTO | |
| 1935-36 | UPPER CANADA COLLEGE | |
| 1936-37 | EARL HAIG SS | |
| 1937-38 | ACADIANS | |
| 1938-39 | COLUMBUS BOYS CLUB | |
| 1939-40 | ARLINGTONS | |
| 1940-41 | ST CLAIR | |
| 1941-42 | TALMACS | |
| 1942-43 | COLUMBUS BOYS CLUB | |
| 1943-44 | COLUMBUS BOYS CLUB | |
| 1944-45 | GLENDALE PHARMACY | |
| 1945-46 | HOUTING RAMBLERS | |
| 1946-47 | CROTHERS BULLDOZERS | |
| 1947-48 | STONEYS | |
| 1948-49 | MARLBORO HC | |
| 1949-50 | DOVERS | ST CLAIR YMCA |
| 1950-51 | IMPERIAL OPTICAL | REGENT AC |
| 1951-52 | DOWNSVIEW | REGENT AC |
| 1952-53 | NORTH YORK FLYERS | PRICES |
| 1953-54 | B&W CIGAR | OAKRIDGE LEGION |
| 1954-55 | DOWNSVIEW CANADIENS | CITY BUICK |
| 1955-56 | DE LA SALLE | WESTLAKE MOTORS |
| 1956-57 | NORTH YORK LEAFS | NO SERIES |
| 1957-58 | CONCORD RANGERS | NO SERIES |
| 1958-59 | DE LA SALLE | EAST YORK HC |
| 1959-60 | DE LA SALLE | WEXFORD |
| 1960-61 | DE LA SALLE | ST CLAIR UNITED |
| 1961-62 | ST MICHAELS | BLYTHWOOD BAPTIST |
| 1962-63 | NEIL McNEIL | DELL CONSTRUCTION |
| 1963-64 | DORSET PARK | NO SERIES |
| 1964-65 | WHITFIELD PACKERS | NO SERIES |
| 1965-66 | DORSET PARK | WEST HILL HC |
| 1966-67 | NO SERIES | CANADIAN TIRE |
| 1967-68 | WEXFORD McALPINES | CITY SERVICE TED REEVE |
| 1968-69 | DORSET PARK HC | SOMMERVILLE |
| 1969-70 | MARLBOROS HC | RADCO LTD |
| 1970-71 | MARLBOROS HC | TED REEVE |
| YEAR | AA | B | C |
| 1971-72 | MARLBOROS HC | TED REEVE | QUEENSWAY |
| 1972-73 | DORSET PARK | QUEENSWAY | QUEENSWAY |
| 1973-74 | NO RECORD | NO RECORD | NO RECORD |
| 1974-75 | WEXFORD | NORTH TORONTO | TED REEVE |
| 1975-76 | WEXFORD | WESTON | NO SERIES |
| 1976-77 | NO RECORD | NO RECORD | NO RECORD |
| 1977-78 | ROYAL YORK | TORONTO OLYMPICS |
| YEAR | MAJOR | A |
| 1978-79 | DON MILLS | NORTH YORK FLAMES |
| 1979-80 | NORTH YORK FLAMES | LIDO BRUINS |
| 1980-81 | DORSET PARK | MISSISSAUGA TERRIERS |
| 1981-82 | WEXFORD | EAST YORK |
| 1982-83 | MISSISSAUGA REPS | MISSISSAUGA NORTH STARS |
| 1983-84 | WEXFORD | WARREN PARK |
| 1984-85 | GOULDING PARK | MISSISSAUGA JETS |
| 1985-86 | GOULDING PARK | MISSISSAUGA BRAVES |
| 1986-87 | VILLAGERS | YORK TOROS |
| 1987-88 | VILLAGERS | ROYAL YORK RANGERS |
| 1988-89 | MISSISSAUGA NORTH STARS | |
| 1989-90 | YORK TOROS | |
| 1990-91 | GOULDING PARK | |
| 1991-92 | MISSISSAUGA NORTH STARS | |
| 1992-93 | MISSISSAUGA JETS | |
| 1993-94 | GOULDING PARK | |
| 1994-95 | NO RECORD | |
| 1995-96 | ETOBICOKE EAGLES | |
| 1996-97 | MISSISSAUGA NORTH STARS | |
| 1997-98 | NO RECORD | |
| 1998-99 | MISSISSAUGA NORTH STARS | |
| 1999-2000 | MISSISSAUGA NORTH STARS | |
| 2000-01 | MISSISSAUGA NORTH STARS | |
| 2001-02 | SCARBORO YOUNG BRUINS |
| YEAR | AAA |
| 2002-03 | SCARBORO YOUNG BRUINS |
| 2003-04 | LEASIDE KINGS |
| 2004-05 | SCARBORO YOUNG BRUINS |
| 2005-06 | HUMBERVIEW HUSKIES |
| 2006-07 | SCARBORO YOUNG BRUINS |
| 2007-08 | HUMBERVIEW HUSKIES |
| 2008-09 | HUMBERVIEW HUSKIES |
| 2009-10 | MISSISAUGA BRAVES |
| 2010-11 | MISSISSAUGA JETS |
| 2011-12 | HUMBERVIEW HUSKIES |
| 2012-13 | HUMBERVIEW HUSKIES |
| 2013-14 | WEST MALL LIGHTNING |
| 2014-15 | MISSISSAUGA BRAVES |
| 2015-16 | MISSISSAUGA BRAVES |
| 2016-17 | TORONTO COLTS |
