Western Ontario Soccer League
Cup Winners
Ontario Cup
| 2015 | Marconi |
| 2014 | Marconi |
| 2012 | AEK Olympians |
| 2010 | AEK Olympians |
| 2008 | AEK Olympians |
| 2002 | Portuguese |
| 1978 | Marconi |
| 1955 | Marconi |
League Cup
| 2023 | Jagiellonia |
| 2022 | London Croatia |
| 2021 | Not awarded |
| 2020 | Not awarded |
| 2019 | Marconi |
| 2018 | Marconi |
| 2017 | Marconi |
| 2016 | Jagiellonia |
| 2015 | Marconi |
| 2014 | Marconi |
| 2013 | Filial Benfica SC |
| 2012 | AEK Olympians |
| 2011 | Croatia |
| 2010 | AEK Olympians |
| 2009 | AEK Olympians |
| 2008 | AEK Olympians |
| 2007 | AEK Olympians |
| 2006 | White Eagles |
| 2005 | Portuguese |
| 2004 | St. Thomas |
| 2003 | AEK Olympics |
| 2002 | Portuguese |
| 2001 | Benfica |
| 2000 | Hungarians |
| 1999 | Portuguese |
| 1998 | Croatia |
| 1997 | Portuguese |
| 1996 | Benfica |
| 1995 | Portuguese |
| 1994 | London City |
| 1993 | Portuguese |
| 1992 | St. Thomas |
| 1991 | Norfolk |
| 1990 | Panhellenic |
| 1989 | White Eagles |
| 1988 | Hungarians |
| 1987 | St. Thomas |
| 1986 | Chatham |
| 1985 | Ingersoll |
| 1984 | Portuguese |
| 1983 | Curinga |
| 1982 | Ingersoll |
| 1981 | Ingersoll |
| 1980 | St. Thomas A |
| 1979 | Marconi |
| 1978 | Marconi |
| 1977 | Roma |
| 1976 | London Celtic |
| 1975 | London Celtic |
| 1974 | Marconi-Inter |
| 1973 | Croatia |
| 1972 | Stratford |
| 1971 | Stratford |
| 1970 | Ingersoll |
| 1969 | Olympians |
| 1968 | Marconi |
| 1967 | Marconi |
| 1966 | Marconi |
| 1965 | Germans |
| 1964 | Marconi |
| 1963 | Queens Royals |
| 1962 | Germans |
| 1961 | Ingersoll Mikes |
| 1960 | Italo Canadians |
Division Cups
| Premier | First | Second | Third | Fourth |
| 2023 | Jagiellonia | African Carib | Serbs | Norfolk | Brazukas |
| 2022 | Jagiellonia | English | Germans | Strathroy | Woodstock |
| 2021 | Not awarded | Not awarded | Not awarded | Not awarded | Not awarded |
| 2020 | Not awarded | Not awarded | Not awarded | Not awarded | Not awarded |
| 2019 | Olympians | English | English | LS Croatia | Strathroy |
| 2018 | Jagiellonia | Taxandria | Carib Stars | African Carib FC | African Car |
| 2017 | Marconi | Sarnia FC | Germans | African Carib FC | LS Croatia |
| 2016 | Marconi | Wallaceburg | Chatham | African Carib FC | Portuguese |
| 2015 | Marconi | Wallaceburg | Chatham | English | Germans |
| Premier | First | Second | Third | Fourth E | Fourth W | Fourth |
| 2014 | Croatia | English | Croatia | English | Germans | St.Columban | St. Columban |
| 2013 | AEK Olympians | Scottish | St. Columban | Pameer | St. Thomas | Exeter | St. Thomas |
| 2012 | AEK Olympians | English | Sarnia | Taxandria | LAC Juventus | Oakridge | LAC Juventus |
| 2011 | AEK Olympians | Portuguese | St. Thomas | Norwest | Marconi | Pachuca | Marconi |
| 2010 | St. Thomas | Marconi | Simcoe | St. Columban | Woodstock | Middlesex | Stathroy |
| Premier | First | Second | Third E | Third W | Third C | Third |
| 2009 | AEK Olympians | Chatham | Portuguese | St. Columban | Middlesex | Taxandria | |
| 2008 | AEK Olympians | Benfica | Wallaceburg | St. Thomas | Marconi | Middlesex | |
| 2007 | Benfica | Bosnia | Benfica | London Renegades | Middlesex | | Colombia |
| 2006 | Portuguese | London City | Sarnia Fury | Delhi Athletics | English F.C. | | |
| Premier | First | Second | Third | U-21 | Rec |
| 2005 | AEK Olympics | Marconi | Portuguese | Sarnia Fury | Bluewater | Ingersoll |
| 2004 | Portuguese | White Eagles | Hispanos | Benfica | Sarnia Fury | |
| 2003 | Portuguese | Croatia | Ingersoll | Strathroy PC B | | |
| 2002 | Portuguese | White Eagles | Marconi B | Curinga | | |
| 2001 | Portuguese | NFC Porto | Croatia | Exeter Fury | | |
| 2000 | Marconi | AEK London | Ingersoll | Portuguese B | | |
| 1999 | Portuguese | Wallaceburg | Serbs | Strathroy PC B | | |
| 1998 | Croatia | Norfolk | Benfica B | AEK Olympians | | |
| 1997 | Portuguese | Croatia | Bosnia | | | |
| 1996 | Portuguese | Norfolk | St. Columban | | | |
| 1995 | London City | Strathroy PC | Benfica | | | |
| 1994 | St. Thomas | Panhellenic | Petrolia | | | |
| 1993 | St. Thomas | London City | Panhellenic | | | |
| 1992 | White Eagles | Hungarians | Dante | | | |
| 1991 | White Eagles | St. Thomas | Dante | | | |
| 1990 | Croatia | Woodstock | Wallaceburg | | | |
| 1989 | Croatia | Bluewater | Simcoe Lusos | | | |
| 1988 | White Eagles | Panhellenic | Simcoe Lusos | | | |
| Level I | Level II |
| 1987 | Curinga | Latinos |
| 1986 | Delhi Athletics | Chatham |
| 1985 | Woodstock | Germans |
| 1984 | Croatia | Croatia B |
| 1983 | Croatia | Bluewater |
| 1982 | St. Columban | Woodstock |
| 1981 | Portuguese | London City U-19 |
| First | Second | Third | Fourth |
| 1980 | Marconi | St Thomas | Ingersoll | St. Bartalomeo |
| 1979 | Hungarians | London United | Yugoslavs | Slavia |
| 1978 | Marconi | Oakridge | Strathroy NC | |
| 1977 | Celtic | Portuguese | Lusitanos United | |
| 1976 | Marconi | Hungarians | St. Columban | |
| 1975 | Scottish | London United | Grand Bend | |
| 1974 | Scottish | White Eagles | Goderich United | |
| 1973 | Celtic | Marconi B | Strathroy Ben | |
| 1972 | Scottish | Ingersoll | White Eagles | |
| 1971 | Germans | Scottish | Croatia | |
| 1970 | Olympians | Croatia | Woodstock | |
| 1969 | | Roma | Croatia | |
| 1968 | Marconi | Celtic | Olympians | |
| 1967 | Marconi | Celtic | Sarnia (Dante) | |
| 1966 | Marconi | Germans B | Germans B | |
| 1965 | Dutch Lions | Sarnia B | Stratford | |
| 1964 | Marconi | Croatia | | |
| 1963 | QR Woodstock | | | |
| 1962 | Dutch Lions | | | |
| 1961 | Dutch Lions | | | |
| 1960 | Dutch Lions | | | |
| 1959 | Dutch Lions | | | |
| 1958 | Stratford FB | | | |
| 1957 | Sarnia (Dante) | | | |
| 1956 | Sarnia (Dante) | | | |
