| 1 Oct 2009 @ 17:00 | | Toronto Maple Leafs |  | 3 | - | 4 |  | Montreal Canadiens | National Hockey League2009-10-01T17:00:00-07:00Toronto Maple Leafs v Montreal Canadiens | Air Canada Centre, Toronto, ON, Canada |
| 31 Oct 2009 @ 17:00 | | Montreal Canadiens |  | 5 | - | 4 |  | Toronto Maple Leafs | National Hockey League2009-10-31T17:00:00-07:00Montreal Canadiens v Toronto Maple Leafs | Bell Centre, Montreal, QC, Canada |
| 1 Dec 2009 @ 16:30 | | Montreal Canadiens |  | 0 | - | 3 | | Toronto Maple Leafs | National Hockey League2009-12-01T16:30:00-08:00Montreal Canadiens v Toronto Maple Leafs | Bell Centre, Montreal, QC, Canada |
| 26 Dec 2009 @ 16:00 | | Toronto Maple Leafs | | 2 | - | 3 |  | Montreal Canadiens | National Hockey League2009-12-26T16:00:00-08:00Toronto Maple Leafs v Montreal Canadiens | Air Canada Centre, Toronto, ON, Canada |
| 20 Mar 2010 @ 17:00 | | Toronto Maple Leafs |  | 3 | OT | 2 | | Montreal Canadiens | National Hockey League2010-03-20T17:00:00-07:00Toronto Maple Leafs v Montreal Canadiens | Air Canada Centre, Toronto, ON, Canada |
| 10 Apr 2010 @ 17:00 | | Montreal Canadiens |  | Vs | | Toronto Maple Leafs | National Hockey League2010-04-10T17:00:00-07:00Montreal Canadiens v Toronto Maple Leafs | Bell Centre, Montreal, QC, Canada |
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| 7 Oct 2010 @ 16:00 | | Toronto Maple Leafs | | Vs | | Montreal Canadiens | National Hockey League2010-10-07T16:00:00-07:00Toronto Maple Leafs v Montreal Canadiens | Air Canada Centre, Toronto, ON, Canada |
| 20 Nov 2010 @ 15:00 | | Montreal Canadiens | | Vs | | Toronto Maple Leafs | National Hockey League2010-11-20T15:00:00-08:00Montreal Canadiens v Toronto Maple Leafs | Bell Centre, Montreal, QC, Canada |
| 11 Dec 2010 @ 15:00 | | Toronto Maple Leafs | | Vs | | Montreal Canadiens | National Hockey League2010-12-11T15:00:00-08:00Toronto Maple Leafs v Montreal Canadiens | Air Canada Centre, Toronto, ON, Canada |
| 12 Feb 2011 @ 15:00 | | Montreal Canadiens | | Vs | | Toronto Maple Leafs | National Hockey League2011-02-12T15:00:00-08:00Montreal Canadiens v Toronto Maple Leafs | Bell Centre, Montreal, QC, Canada |
| 24 Feb 2011 @ 15:30 | | Montreal Canadiens | | Vs | | Toronto Maple Leafs | National Hockey League2011-02-24T15:30:00-08:00Montreal Canadiens v Toronto Maple Leafs | Bell Centre, Montreal, QC, Canada |
| 9 Apr 2011 @ 16:00 | | Toronto Maple Leafs |  | Vs | | Montreal Canadiens | National Hockey League2011-04-09T16:00:00-07:00Toronto Maple Leafs v Montreal Canadiens | Air Canada Centre, Toronto, ON, Canada |
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Montreal Canadiens