Peewee Champions
| YEAR | A | B | C |
| 1943-44 | ETOBICOKE AC | ||
| 1944-45 | ETOBICOKE AC | ||
| 1945-46 | NORTH TORONTO KINSMEN | ||
| 1946-47 | ST JOSEPHS | ||
| 1947-48 | ETOBICOKE AC | ||
| 1948-49 | SHOPSY’S – MARLBOROS | ||
| 1949-50 | SHOPSY’S – MARLBOROS | LEASIDE LIONS | |
| 1950-51 | LEASIDE LIONS | SIMMONS JEWELLERS | |
| 1951-52 | SHOPSY’S – MARLBOROS | NO SERIES | |
| 1952-53 | SHOPSY’S – MARLBOROS | LEASIDE LIONS | |
| 1953-54 | SHOPSY’S – MARLBOROS | NO SERIES | |
| 1954-55 | TED’S PALS | SHARPES SILVER DOLLARS | |
| 1955-56 | TED’S PALS | METAL ART RAILING | |
| 1956-57 | SHOPSY’S – MARLBOROS | ST THOMAS AQUINAS | |
| 1957-58 | FAUSTINA | DAVE’S WHITE ROSE | |
| 1958-59 | HONEST ED’S | HUMBER VALLEY RAMS | |
| 1959-60 | SCARBORO LIONS | SCARBORO K OF C | |
| 1960-61 | DILEO COSTRUCTION | HUMBER VALLEY RAMS | |
| 1961-62 | SHOPSY’S – MARLBOROS | BROMPTON PETES | |
| 1962-63 | NORTH YORK KNIGHTS | SWEETS IGA | |
| 1963-64 | TORONTO TORRIDS | NORTH ETOBICOKE | |
| 1964-65 | MINE SAFETY APPLIANCES | NORTH ETOBICOKE | |
| 1965-66 | SHOPSY’S – MARLBOROS | HENDERSON RANGERS | |
| 1966-67 | YORK STEEL | ADMIRAL SANITATION | |
| 1967-68 | YOUNG NATS | PERKINS DEASELS | |
| 1968-69 | SHOPSY’S – MARLBOROS | AVENUE ROAD LIONS | |
| 1969-70 | TORONTO OLYMPIC | QUEENSWAY | REXDALE LIONS |
| 1970-71 | SHOPSY’S – MARLBOROS | WEXFORD SHA | RALEIGH AUTO BODY |
| YEAR | AA | A | B | C |
| 1971-72 | SHOPSY’S – MARLBOROS | DIXIE ROYALS | TED REEVE | |
| 1972-73 | DON VALLEY | FAUSTINA | WARREN PARK | |
| 1973-74 | NO RECORD | NO RECORD | NO RECORD | |
| 1974-75 | SHOPSY’S – MARLBOROS | MISSISSAUGA REPS | DOWNSVIEW | GOULDING PARK |
| 1975-76 | SHOPSY’S – MARLBOROS | MISSISSAUGA REPS | ROYAL YORK | TORONTO OLYMPICS |
| 1976-77 | NO RECORD | NO RECORD | NO RECORD | |
| 1977-78 | MISSISSAUGA REPS | GOULDING PARK | VILLAGERS |
| YEAR | MAJOR | AA | A |
| 1978-79 | MARLBOROS | NORTH YORK FLAMES | TED REEVE |
| 1979-80 | MARLBOROS | EAST ENDERS | OLYMPICS |
| 1980-81 | RED WINGS | MISSISSAGA N-STARS | HILLCREST |
| 1981-82 | MISSISSAUGA REPS | GOULDING PARK | LEASIDE KINGS |
| 1982-83 | MARLBOROS | TORONTO AEROS | WEST TORONTO PIRATES |
| 1983-84 | MISSISSAUGA REPS | MISSISSAGA BRAVES | WARREN PARK |
| 1984-85 | YOUNG NATS | MISSISSAUGA JETS | TED REEVE |
| 1985-86 | WEXFORD | MISSISSAUGA JETS | WEST MALL |
| 1986-87 | DON MILLS | TORONTO AEROS | WEST MALL |
| 1987-88 | MISSISSAUGA REPS | HILLCREST | HUMBERVIEW |
| 1988-89 | RED WINGS | GOULDING PARK | TED REEVE |
| 1989-90 | MISSISSAUGA BLACK HAWK | NORTH TORONTO | TORONTO AEROS |
| 1990-91 | MARLBOROS | MISSISSAUGA TERRIERS | SCARBORO YOUNG BRUINS |
| 1991-92 | WEXFORD | MISSISSAUGA N-STARS | WILLOWDALE BLACK HAWK |
| 1992-93 | RED WINGS | MISSISSAUGA BRAVES | ROYALS |
| 1993-94 | RED WINGS | MISSISSAUGA BRAVES | WILLOWDALE BLACK HAWK |
| 1994-95 | NO RECORD | NO RECORD | NO RECORD |
| 1995-96 | RED WINGS | NORTH TORONTO | HORNETS |
| 1996-97 | NORTH YORK CANADIENS | NORTH TORONTO | TORONTO COLTS |
| 1997-98 | NO RECORD | NO RECORD | NO RECORD |
| 1998-99 | NORTH YORK CANADIENS | MARKHAM ISLANDERS | VAUGHAN PANTHERS |
| 1999-2000 | MARLBOROS | SCARBORO YOUNG BRUIN | |
| 2000-01 | MARLBOROS | NORTH TORONTO | WESTON HAWKS |
| YEAR | AAA | AA | A |
| 2001-02 | JR CANADIENS | YORK TOROS | DOWNSVIEW BEAVERS |
| 2002-03 | VAUGHAN KINGS | MISSISSAUGA BRAVES | VAUGHAN RANGERS |
| 2003-04 | MISSISSAUGA REPS | WESTON HAWKS | VAUGHAN RANGERS |
| 2004-05 | JR CANADIENS | MISSISSAUGA JETS | TORONTO AEROS |
| 2005-06 | MARLBOROS | ETOBICOKE CANUCKS | WEST MALL |
| 2006-07 | MARLBOROS | NORTH YORK KNIGHTS | VAUGHAN RANGERS |
| 2007-08 | RED WINGS | NORTH YORK KNIGHTS | LEASIDE FLAMES |
| 2008-09 | VAUGHAN KINGS | MISSISSAUGA BRAVES | TORONTO COLTS |
| 2009-10 | MARLBOROS | MISSISSAUGA TERRIERS | LEASIDE FLAMES |
| 2010-11 | MARLBOROS | MISSISSAUGA JETS | VAUGHAN PANTHERS |
| 2011-12 | YOUNG NATS | MISSISSAUGA BRAVES | VAUGHAN RANGERS |
| 2012-13 | MISSISAUGA REBELS | TED REEVE | WILLOWDALE BLACKHAWKS |
| 2013-14 | TORONTO MARLBOROS | MISSISSAUGA JETS | NORTH YORK KNIGHTS |
| 2014-15 | TORONTO MARLBOROS | STREETSVILLE TIGERS | TORONTO WOLVERINES |
| 2015-16 | LEASIDE FLAMES | MISSISSAUGA TERRIERS | DON MILLS FLYERS |
| 2016-17 | WEST HILL GOLDEN HAWKS | VAUGHAN RANGERS | TORONTO JR. CANADIENS |
