| Sep 24, 1999 Fri | | Plymouth | Sarnia | Ustrnul-Berti
Ramsay-MacIver
Ramsay-McMorrow |
| Sep 25, 1999 Sat | | Oshawa | Plymouth | Brawl at 38:50
Demidov-Ramsay
Passmore-Newman |
| Oct 1, 1999 Fri | | Sudbury | Plymouth | McGrattan-Ustrnul |
| Oct 2, 1999 Sat | | Plymouth | Barrie | Ramsay-Connell
Newman-Danton
Wray-Barnes |
| Oct 3, 1999 Sun | | Plymouth | Mississauga | Ramsay-Coughlin |
| Oct 8, 1999 Fri | | Brampton | Plymouth | Harrison-Lalonde
MacSweyn-Holdridge
Maleyko-Surma |
| Oct 9, 1999 Sat | | St. Michael's | Plymouth | Farquharson-Ustrnul
Gough-Lalonde |
| Oct 10, 1999 Sun | | Plymouth | Windsor | Ramsay-Sewell
Kurka-Linnik
Newman-Ridout |
| Oct 15, 1999 Fri | | Windsor | Plymouth | Add Fight |
| Oct 16, 1999 Sat | | Barrie | Plymouth | Add Fight |
| Oct 21, 1999 Thu | | Plymouth | North Bay | Surma-Reynolds |
| Oct 22, 1999 Fri | | Plymouth | Sudbury | Add Fight |
| Oct 24, 1999 Sun | | Plymouth | Sault Ste. Marie | Surma-Spurr
Ramsay-Browne
Newman-Healy |
| Oct 29, 1999 Fri | | Sarnia | Plymouth | McMorrow-Ramsay
Burnham-Kiser |
| Oct 30, 1999 Sat | | Sault Ste. Marie | Plymouth | Zafiris-Ramsay |
| Oct 31, 1999 Sun | | Plymouth | Sarnia | Gooldy-Berti |
| Nov 5, 1999 Fri | | Plymouth | Oshawa | Add Fight |
| Nov 6, 1999 Sat | | Plymouth | Belleville | Gooldy-Bertran
Ramsay-Policelli
Newman-Cheechoo |
| Nov 7, 1999 Sun | | Plymouth | St. Michael's | Ustrnul-Farquharson
Holdridge-Simpson
Thompson-Mizzi |
| Nov 12, 1999 Fri | | North Bay | Plymouth | Bacon-Kiser
McKay-Surma |
| Nov 13, 1999 Sat | | Kitchener | Plymouth | Peters-Ustrnul (6.3)
Milanovic-Ustrnul (5) |
| Nov 18, 1999 Thu | | Plymouth | Peterborough | Add Fight |
| Nov 19, 1999 Fri | | Plymouth | Kingston | Newman-Clouthier |
| Nov 21, 1999 Sun | | Plymouth | Ottawa | Fisher-Bell
Kiser-Galbraith |
| Nov 24, 1999 Wed | | Plymouth | Owen Sound | Add Fight |
| Nov 25, 1999 Thu | | Plymouth | Brampton | Add Fight |
| Nov 27, 1999 Sat | | Peterborough | Plymouth | Carkner-Ramsay
Brawl at 36:17 |
| Nov 28, 1999 Sun | | Plymouth | Windsor | Ramsay-Stayzer
Surma-Kennedy
Ramsay-Sewell
Barker-Chapman |
| Dec 4, 1999 Sat | | London | Plymouth | Add Fight |
| Dec 5, 1999 Sun | | Plymouth | Owen Sound | Thompson-Zalba |
| Dec 10, 1999 Fri | | Sault Ste. Marie | Plymouth | Chapman-Kiser
Browne-Ramsay
Gibson-Gooldy |
| Dec 11, 1999 Sat | | Erie | Plymouth | Lagace-Williams
unknown-Newman |
| Dec 12, 1999 Sun | | Plymouth | Kitchener | Add Fight |
| Dec 17, 1999 Fri | | Plymouth | Erie | Brawl at 36:41
Fitzgerald-Yeo
Newman-Rupp |
| Dec 18, 1999 Sat | | Plymouth | Erie | Add Fight |
| Dec 28, 1999 Tue | | Erie | Plymouth | Moher-Surma |
| Dec 30, 1999 Thu | | Kitchener | Plymouth | Gagnon-Fitzgerald
Milanovic-Ramsay |
| Jan 5, 2000 Wed | | Guelph | Plymouth | House-Lalonde |
| Jan 7, 2000 Fri | | Plymouth | London | Add Fight |
| Jan 8, 2000 Sat | | Belleville | Plymouth | Policelli-Ramsay |
| Jan 13, 2000 Thu | | Plymouth | Windsor | Ramsay-Stayzer
Gooldy-Mahon
Cava-Chapman
Newman-Sewell
Williams-Ott |
| Jan 14, 2000 Fri | | Sault Ste. Marie | Plymouth | Gibson-Lalonde |
| Jan 15, 2000 Sat | | Brampton | Plymouth | McLaughlin-Lalonde |
| Jan 21, 2000 Fri | | Plymouth | Sault Ste. Marie | Ramsay-Bennett
Brawl at 38:56 |
| Jan 22, 2000 Sat | | Owen Sound | Plymouth | Goldie-Newman
Jacina-Jarrett
Goldie-Ustrnul
Kowalski-Ramsay
Brawl at 52:41
Blanchard-Kiser |
| Jan 28, 2000 Fri | | Windsor | Plymouth | Finnegan-Ustrnul |
| Jan 29, 2000 Sat | | Ottawa | Plymouth | Add Fight |
| Feb 4, 2000 Fri | | Plymouth | Sault Ste. Marie | Cava-Jones |
| Feb 5, 2000 Sat | | Guelph | Plymouth | King-Kiser |
| Feb 8, 2000 Tue | | Sarnia | Plymouth | Berti-Cava
Burnham-Ustrnul |
| Feb 11, 2000 Fri | | Plymouth | Kitchener | Ramsay-McMorrow (7.2) |
| Feb 12, 2000 Sat | | Mississauga | Plymouth | Page-Ramsay
Ketcheson-Nistas
Jarram-Gooldy |
| Feb 13, 2000 Sun | | Erie | Plymouth | Rozendal-Ramsay
Brawl at 58:36 |
| Feb 17, 2000 Thu | | Plymouth | Guelph | Vernarsky-Brown
Robichaud-Forbes |
| Feb 18, 2000 Fri | | Sarnia | Plymouth | Add Fight |
| Feb 19, 2000 Sat | | London | Plymouth | Jancevski-Lalonde |
| Feb 24, 2000 Thu | | Plymouth | Brampton | Lalonde-Rowan |
| Feb 26, 2000 Sat | | Windsor | Plymouth | unknown-Ramsay
Mahon-Gooldy
Ott-Fitzgerald |
| Feb 27, 2000 Sun | | Plymouth | Windsor | Ustrnul-Sewell |
| Mar 1, 2000 Wed | | Plymouth | Erie | Add Fight |
| Mar 3, 2000 Fri | | Plymouth | London | Add Fight |
| Mar 7, 2000 Tue | | Kingston | Plymouth | Avery-McBride
Tennant-Ustrnul
Lisabeth-Surma
Clouthier-Gooldy
Scotland-Kiser
Seguin-Weiss |
| Mar 11, 2000 Sat | | London | Plymouth | Maracle-Surma
Turner-Lalonde
Maracle-Cava
Sullivan-Ustrnul |
| Mar 12, 2000 Sun | | Owen Sound | Plymouth | Campbell-Newman |
| Mar 17, 2000 Fri | | Plymouth | Guelph | Ustrnul-McCormick
Cava-McCormick |
| Mar 18, 2000 Sat | | Windsor | Plymouth | Rawski-Lalonde
Ridout-Gooldy
Sewell-Newman
Chapman-Cava
Courtney-Ustrnul
Sewell-Lalonde
Stayzer-Kiser |
| Mar 19, 2000 Sun | | Plymouth | Sarnia | Cava-Newbury
Surma-Jamieson |
| Mar 24, 2000 Fri | | Plymouth | London | Add Fight |
| Mar 25, 2000 Sat | Round 1 | Game 1 | Guelph | Plymouth | Dallman-Fitzgerald |
| Mar 27, 2000 Mon | Round 1 | Game 2 | Plymouth | Guelph | Add Fight |
| Mar 29, 2000 Wed | Round 1 | Game 3 | Guelph | Plymouth | Stephens-Kiser
King-Ramsay (9.5)
Forbes-Ustrnul
McCormick-Fitzgerald |
| Mar 31, 2000 Fri | Round 1 | Game 4 | Plymouth | Guelph | Add Fight |
| Apr 1, 2000 Sat | Round 1 | Game 5 | Guelph | Plymouth | Add Fight |
| Apr 4, 2000 Tue | Round 1 | Game 6 | Plymouth | Guelph | Add Fight |
| Apr 8, 2000 Sat | QF | Game 1 | Windsor | Plymouth | Add Fight |
| Apr 10, 2000 Mon | QF | Game 2 | Plymouth | Windsor | Ramsay-Sinacori |
| Apr 12, 2000 Wed | QF | Game 3 | Windsor | Plymouth | Add Fight |
| Apr 14, 2000 Fri | QF | Game 4 | Plymouth | Windsor | Add Fight |
| Apr 15, 2000 Sat | QF | Game 5 | Windsor | Plymouth | Add Fight |
| Apr 22, 2000 Sat | SF | Game 1 | Sault Ste. Marie | Plymouth | Milanovic-Cava
MacMillan-Fitzgerald
Bennett-Jarrett
Jones-Newman
Healy-Newman |
| Apr 25, 2000 Tue | SF | Game 2 | Plymouth | Sault Ste. Marie | Add Fight |
| Apr 26, 2000 Wed | SF | Game 3 | Plymouth | Sault Ste. Marie | Add Fight |
| Apr 28, 2000 Fri | SF | Game 4 | Sault Ste. Marie | Plymouth | Add Fight |
| Apr 29, 2000 Sat | SF | Game 5 | Sault Ste. Marie | Plymouth | Chapman-Vernarsky |
| May 4, 2000 Thu | Final | Game 1 | Plymouth | Barrie | Add Fight |
| May 7, 2000 Sun | Final | Game 2 | Barrie | Plymouth | Henrich-Lalonde |
| May 8, 2000 Mon | Final | Game 3 | Barrie | Plymouth | Barnes-Cava
Hwodeky-Kiser |
| May 10, 2000 Wed | Final | Game 4 | Plymouth | Barrie | Add Fight |
| May 12, 2000 Fri | Final | Game 5 | Barrie | Plymouth | Add Fight |
| May 14, 2000 Sun | Final | Game 6 | Plymouth | Barrie | Add Fight |
| May 16, 2000 Tue | Final | Game 7 | Barrie | Plymouth | Add Fight |