Midget Champions
| YEAR | A | B |
| 1915-16 | ST MARYS | |
| 1916-17 | CENTURY ROVERS | |
| 1917-18 | PARKVIEWS | |
| 1918-19 | PARKVIEWS | |
| 1919-20 | MELVIRS | |
| 1920-21 | MELVIRS | |
| 1921-22 | AURA LEE | |
| 1922-23 | DANFORTHS | |
| 1923-24 | BELLEFAIRS | |
| 1924-25 | DANFORTHS | |
| 1925-26 | DANFORTHS | |
| 1926-27 | NORTH TORONTO | |
| 1927-28 | MAITLANDS | |
| 1928-29 | MAITLANDS | |
| 1929-30 | UNIVERSITY SCHOOLS | |
| 1930-31 | NATIVE SONS | |
| 1931-32 | NATIONAL SEA FLEAS | |
| 1932-33 | MARLBOROS HC | |
| 1933-34 | UNIVERSITY SCHOOLS | |
| 1934-35 | COLUMBUS BOYS CLUB | |
| 1935-36 | ST CYPRIANS | |
| 1936-37 | RUNNYMEDE CI | |
| 1937-38 | COLUMBUS BOYS CLUB | |
| 1938-39 | ST MICHAELS | |
| 1939-40 | SHAMROCKS HC | |
| 1940-41 | SHAMROCKS HC | |
| 1941-42 | ST MICHAELS | |
| 1942-43 | CHEWIES ACES | |
| 1943-44 | ST MICHAELS | |
| 1944-45 | ST MICHAELS | |
| 1945-46 | MARLBOROS HC | |
| 1946-47 | ST MICHAELS | |
| 1947-48 | BEACHES LIONS | |
| 1948-49 | ST MICHAELS | |
| 1949-50 | COOKSVILLE B&T | DE LA SALLE |
| 1950-51 | DE LA SALLE | CORNER BOYS |
| YEAR | MAJOR | A | B |
| 1951-52 | RHODES AC | MAROON AC | GREEN ACRES |
| 1952-53 | DOWNSVIEW HC | SCARBORO RANGERS | AVENUE ROAD LIONS |
| 1953-54 | DOWNSVIEW CANADIENS | DE LA SALLE | UPPER CANADA COLLEGE |
| 1954-55 | MARLBORO HC | DE LA SALLE | O.L.P.H. (CYO) |
| 1955-56 | MARLBORO HC | SHELTONS GROCERY | NO SERIES |
| 1956-57 | MARLBORO HC | HUSTLERS BIBLE CLASS | NO SERIES |
| 1957-58 | MARLBORO HC | QUEENSWAY RODGERS | DE LA SALLE |
| 1958-59 | MARLBORO HC | KENSCOTT HC | QUEENSWAY RODGERS |
| 1959-60 | MARLBORO HC | TORONTO RAMBLERS | REDMEN |
| 1960-61 | MARLBORO HC | NO SERIES | SCARBORO GLASS |
| 1961-62 | MARLBORO HC | NO SERIES | NEIL McNEIL HS |
| 1962-63 | BICK’S PICKLES | MICHAEL POWER HS | NO SERIES |
| 1963-64 | MARLBORO HC | HV DUFFERIN CONST. | NO SERIES |
| 1964-65 | MARLBORO HC | NO SERIES | NO SERIES |
| 1965-66 | LIMESTONE QUARRIES | ST MICHAELS | NEIL McNEIL HS |
| 1966-67 | MARLBORO HC | ST MICHAELS | NEIL McNEIL HS |
| 1967-68 | BUTTER BEEPS | GOULDING PARK | TORONTO ACES |
| 1968-69 | GOULDING PARK | NO SERIES | MESCHINO BANANA |
| YEAR | A | B | C |
| 1969-70 | WESTON DODGERS | GOULDING PARK | CEDAR HILL |
| 1970-71 | TORONTO YOUNG NATS | FOSTERS FIREBIRDS | NEHA |
| YEAR | AA | A |
| 1971-72 | WEXFORD | TED REEVE |
| 1972-73 | MARLBORO HC | WARREN PARK |
| 1973-74 | NO RECORD | NO RECORD |
| 1974-75 | ROYAL YORK RANGERS | MISSISSAUGA REPS |
| 1975-76 | TORONTO YOUNG NATS | MISSISSAUGA REPS |
| 1976-77 | NO RECORD | NO RECORD |
| 1977-78 | WEXFORD | METRO BLACKHAWKS |
| B | C | |
| 1971-72 | ROYAL YORK | |
| 1972-73 | WEST HILL | WEXFORD |
| 1973-74 | NO RECORD | NO RECORD |
| 1974-75 | CANUCKS | TED REEVE |
| 1975-76 | LONG BRANCH | McCORMICK |
| 1976-77 | NO RECORD | NO RECORD |
| 1977-78 | HILLCREST SUMMITS |
| YEAR | MAJOR | AA | A |
| 1978-79 | ST MICHAELS | ROYAL YORK RANGERS | YORKBORO TRAPPERS |
| 1979-80 | NORTH YORK FLAMES | WESTON DUKES | DORSET PARK |
| 1980-81 | WEXFORD | METRO BLACKHAWKS | EAST YORK |
| 1981-82 | MISSISSAUGA REPS | MISSISSAUGA REPS | WARREN PARK |
| 1982-83 | DON MILLS FLYERS | VILLAGERS | THORNHILL ISLANDERS |
| 1983-84 | ST MICHAELS | GOULDING PARK | HUMBER VALLEY |
| 1984-85 | RED WINGS | ROYALS | WEST HILL |
| 1985-86 | RED WINGS | GOULDING PARK | TORONTO DEVILS |
| 1986-87 | MARLBOROS HC | NORTH TORONTO | NO SERIES |
| 1987-88 | RED WINGS | GOULDING PARK | ROYAL YORK |
| 1988-89 | WEXFORD | NORTH TORONTO | WARREN PARK |
| 1989-90 | TORONTO YOUNG NATS | ROYALS | GOULDING PARK |
| 1990-91 | MISSISSAUGA REPS | NORTH TORONTO | WARREN PARK |
| 1991-92 | MISSISAUGA BLACK HAWKS | HILLCREST SUMMITS | NO SERIES |
| 1992-93 | WEXFORD | NORTH TORONTO | SCARBORO STALLIONS |
| 1993-94 | WEXFORD | MISSISAUGA JETS | NO SERIES |
| 1994-95 | NO RECORD | NO RECORD | NO RECORD |
| 1995-96 | NORTH YORK CANADIENS | MISSISAUGA TERRIERS | CLARKSON |
| 1996-97 | WEXFORD | MISSISSAUGA JETS | NO SERIES |
| 1997-98 | NO SERIES | NO SERIES | NO SERIES |
| 1998-99 | NORTH YORK CANADIENS | LEASIDE KINGS | WILLOWDALE BLACKHAWKS |
| 1999-2000 | MISSISSAUGA REPS | MISSISAUGA BRAVES | MARKHAM ISLANDERS |
| 2000-01 | TORONTO YOUNG NATS | HUMBERVIEW HUSKIES | GOULDING PARK |
| 2001-02 | TORONTO YOUNG NATS | WEST MALL LIGHTNING | WILLOWDALE BLACKHAWKS |
| YEAR | AAA | AA | A |
| 2002-03 | MISSISSAUGA REBELS | MISSISSAUGA NORTH STAR | TORONTO PENGUINS |
| 2003-04 | TORONTO MARLBOROS | MISSISSAUGA JETS | ISLANDERS |
| 2004-05 | DON MILLS FLYERS | NORTH TORONTO | ISLANDERS |
| 2005-06 | TORONTO JR CANADIENS | EAST ENDER TICATS | DOWNSVIEW BEAVERS |
| 2006-07 | TORONTO JR CANADIENS | NORTH YORK KNIGHTS | AVALANCHE |
| 2007-08 | VAUGHAN KINGS | NORTH YORK KNIGHTS | NORTH YORK KNIGHTS |
| 2008-09 | TORONTO TITANS | WILLOWDALE BLACKHAWK | TORONTO PENGUINS |
| 2009-10 | MISSISSAUGA REPS | MISSISSAUGA JETS | TORONTO AEROS |
| 2010-11 | MISSISSAUGA REBELS | MISSISSAUGA NORTH STARS | HILLCREST CANADIENS |
| NORTH YORK KNIGHTS | HILLCREST CANADIENS | ||
| 2011-12 | MISSISSAUGA REBELS | NORTH YORK KNIGHTS | DUFFIELD DEVILS |
| STREETSVILLE TIGERS | TORONTO PENGUINS | ||
| 2012-13 | VAUGHAN KINGS | WEST MALL LIGHTNING | TORONTO PENGUINS |
| 2013-14 | TORONTO YOUNG NATIONALS | STREETSVILLE TIGERS | VAUGHAN PANTHERS |
| 2014-15 | TORONTO YOUNG NATIONALS | MISSISSAUGA NORTH STARS | NORTH TORONTO |
| 2015-16 | DUFFIELD DEVILS | MISSISSAUGA JETS | NORTH YORK RANGERS |
| 2016-17 | HILLCREST CANADIENS | MISSISSAUGA JETS | MISSISSAUGA REBELS |
