The Toronto Maple Leafs had their most penalty minutes in a game versus the Canadiens on December 9, 1953, with 98 minutes in the box.

maple leafs most penalty minutes in a regular-season game vs canadiens

	TEAM	PIM	DATE	TM		OPP	RESULT	G	GA	PPG	PPO	OPP PPG	OPP PPO	S	SA
1	Maple Leafs	98	12/9/1953	TOR	vs	MTL	W 3-0	3	0	2		0
2	Maple Leafs	82	1/8/2009	TOR	@	MTL	L 2-6	2	6	1	6	2	8	32	29
3	Maple Leafs	74	12/9/1970	TOR	vs	MTL	W 4-0	4	0	2		0		32	33
4	Maple Leafs	69	3/25/2006	TOR	@	MTL	L 2-6	2	6	1	4	3	7	28	29
5	Maple Leafs	63	12/8/1955	TOR	@	MTL	L 1-3	1	3	0		2		27	34
6	Maple Leafs	58	2/23/1991	TOR	@	MTL	T 3-3	3	3	1	2	1	4	31	29
7	Maple Leafs	51	2/9/2013	TOR	@	MTL	W 6-0	6	0	2	6	0	4	28	37
8	Maple Leafs	47	10/1/2013	TOR	@	MTL	W 4-3	4	3	1	7	0	4	38	37
9	Maple Leafs	44	4/27/2013	TOR	vs	MTL	L 1-4	1	4	1	7	0	6	17	28
10	Maple Leafs	43	12/12/1990	TOR	vs	MTL	W 4-1	4	1	1	4	0	4	28	29
11	Maple Leafs	40	1/7/2017	TOR	vs	MTL	L 3-5	3	5	2	4	2	6	36	31
12	Maple Leafs	40	3/2/1966	TOR	vs	MTL	T 3-3	3	3	2		2		38	36
13	Maple Leafs	40	12/17/1959	TOR	@	MTL	L 2-8	2	8	0		2		31	53
14	Maple Leafs	39	2/14/1953	TOR	vs	MTL	T 2-2	2	2	0		0
15	Maple Leafs	39	11/25/1948	TOR	@	MTL	W 2-0	2	0	0		0
16	Maple Leafs	38	3/12/1936	TOR	@	MTL	W 6-3	6	3	0		0
17	Maple Leafs	37	2/7/2009	TOR	@	MTL	W 5-2	5	2	0	5	1	8	41	33
18	Maple Leafs	37	12/21/1966	TOR	@	MTL	L 2-6	2	6	1		3		26	31
19	Maple Leafs	37	10/30/1963	TOR	vs	MTL	W 6-3	6	3	2		0		30	31
20	Maple Leafs	37	1/11/1944	TOR	vs	MTL	W 5-0	5	0	0		0
21	Maple Leafs	36	11/11/1978	TOR	@	MTL	L 2-3	2	3	0	5	1	6	29	30
22	Maple Leafs	36	3/2/1933	TOR	@	MTL	L 3-4	3	4
23	Maple Leafs	35	11/2/2002	TOR	vs	MTL	L 2-5	2	5	2	6	1	8	32	28
24	Maple Leafs	35	12/12/1981	TOR	vs	MTL	L 2-6	2	6	0	5	2	6	24	36
25	Maple Leafs	35	2/10/1965	TOR	vs	MTL	W 6-2	6	2	1		2		37	26