Ted Lindsay has the most career penalty minutes by a player against a team, with 493 minutes in the box against the Maple Leafs.

	NAME	PIM	OPP	GP	G	A	P	+/-	PPG	PPA	SHG	SHA	GWG	OTG	S	S%	FOW	FO	FOW%	HIT	BKS	TKA	GVA	TOI/GP
1	Ted Lindsay T. Lindsay	493	Maple Leafs	215	70	82	152	-1	21	24	2	0	13	0	41	7.3
2	Tim Hunter T. Hunter	423	Coyotes	71	7	4	11	-6	0	0	0	0	1	0	61	11.5
3	Marty McSorley M. McSorley	412	Flames	66	6	13	19	-5	1	3	1	0	0	0	88	6.8	0	0		2	1	0	2	17:37
4	Tim Hunter T. Hunter	392	Oilers	70	7	4	11	-1	2	0	0	0	0	0	53	13.2
5	Fern Flaman F. Flaman	387	Canadiens	185	4	25	29	-4	0	2	0	0	1	0	18	5.6
6	Bob Probert B. Probert	383	Maple Leafs	65	22	15	37	+6	4	4	0	0	4	0	90	24.4	1	1	100.0	12	0	1	1	10:40
7	Dave Williams D. Williams	376	Flames	74	19	22	41	-10	3	7	0	0	3	0	141	13.5
8	Basil McRae B. McRae	369	Maple Leafs	52	5	7	12	-1	2	1	0	0	0	0	56	8.9
9	Maurice Richard M. Richard	363	Red Wings	199	93	71	164	+1	27	17	0	1	10	0	23	13.0
10	Tim Hunter T. Hunter	359	Kings	75	8	12	20	+13	0	1	0	0	2	0	58	13.8
11	Basil McRae B. McRae	359	Blackhawks	57	6	12	18	-11	2	5	0	0	0	0	49	12.2
12	Ted Lindsay T. Lindsay	359	Canadiens	215	67	82	149	+3	25	27	3	0	12	0	46	8.7
13	Gordie Howe G. Howe	350	Maple Leafs	312	136	180	316	+6	37	69	2	3	25	0	659	8.8
14	Gordie Howe G. Howe	348	Canadiens	313	120	162	282	+1	30	68	2	3	9	0	578	8.7
15	Marty McSorley M. McSorley	347	Canucks	79	11	31	42	+13	0	8	0	1	0	0	118	9.3	0	0		0	0	0	0	11:11
16	Ted Lindsay T. Lindsay	347	Rangers	217	79	114	193	+8	16	30	2	0	13	0	42	7.1
17	Rob Ray R. Ray	343	Canadiens	60	2	3	5	-10	0	0	0	0	0	0	33	6.1	0	0		10	1	4	2	5:25
18	Chris Nilan C. Nilan	341	Whalers	56	14	9	23	+10	1	1	0	0	0	0	74	18.9
19	Ted Lindsay T. Lindsay	326	Bruins	208	76	80	156	+1	15	22	1	0	9	0	35	17.1
20	Tim Horton T. Horton	321	Bruins	229	21	61	82	+42	1	9	0	1	4	0	294	5.1
21	Bill Gadsby B. Gadsby	321	Canadiens	254	33	68	101	-40	8	21	3	2	3	0	122	8.2
22	Shane Churla S. Churla	319	Blackhawks	39	2	6	8	+1	0	1	0	0	0	0	21	9.5
23	Gordie Howe G. Howe	319	Black Hawks	316	169	179	348	-21	45	59	5	1	31	0	657	9.0
24	Chris Nilan C. Nilan	318	Bruins	53	8	13	21	+17	2	0	0	0	0	0	63	12.7
25	Tim Hunter T. Hunter	316	Canucks	67	1	7	8	-5	0	0	0	0	0	0	43	2.3