Between the 1988-89 and 1998-99 seasons, Rob Ray had the most penalty minutes, with 2,529 minutes in the box.

NHL most pims by a player 1988-89 to 1998-99

	NAME	PIM	GP	G	A	P	+/-	PPG	PPA	SHG	SHA	GWG	OTG	S	S%
1	Rob Ray R. Ray	2,529	645	33	38	71	-32	2	1	0	0	3	0	280	11.8
2	Craig Berube C. Berube	2,486	762	49	80	129	-71	2	2	0	0	5	0	529	9.3
3	Tie Domi T. Domi	2,458	558	50	77	127	-41	2	1	0	0	5	0	505	9.9
4	Marty McSorley M. McSorley	2,433	687	82	208	290	-6	13	57	8	12	5	1	1,144	7.2
5	Gino Odjick G. Odjick	2,291	480	50	55	105	-19	6	4	0	0	9	0	566	8.8
6	Dave Manson D. Manson	2,273	802	95	256	351	-19	43	104	3	6	7	1	1,895	5.0
7	Bob Probert B. Probert	2,102	545	101	138	239	-14	24	27	0	0	17	1	765	13.2
8	Shane Churla S. Churla	2,077	437	25	39	64	-52	4	5	0	0	3	0	318	7.9
9	Ken Baumgartner K. Baumgartner	2,053	666	11	38	49	-78	0	0	0	1	1	0	273	4.0
10	Mick Vukota M. Vukota	1,989	556	16	29	45	-36	0	1	0	0	0	0	262	6.1
11	Kris King K. King	1,965	794	62	81	143	-54	0	1	2	2	9	0	738	8.4
12	Mike Peluso M. Peluso	1,951	458	38	52	90	-15	6	2	0	0	2	0	311	12.2
13	Pat Verbeek P. Verbeek	1,911	839	334	357	691	+1	125	130	1	2	45	2	2,144	15.6
14	Kelly Chase K. Chase	1,899	433	17	35	52	-9	0	1	0	0	4	0	218	7.8
15	Ronnie Stern R. Stern	1,874	556	71	81	152	-28	2	1	3	2	9	1	693	10.2
16	Chris Chelios C. Chelios	1,820	807	117	476	593	+180	47	248	9	23	21	0	2,235	5.2
17	Ulf Samuelsson U. Samuelsson	1,817	756	39	184	223	+145	6	38	0	8	7	1	869	4.5
18	Dale Hunter D. Hunter	1,780	805	161	342	503	-18	61	104	1	5	28	3	1,075	15.0
19	Lyle Odelein L. Odelein	1,762	648	32	133	165	+92	9	38	1	2	4	0	682	4.7
20	Rick Tocchet R. Tocchet	1,719	712	331	361	692	+38	107	109	10	3	38	2	2,038	16.2
21	Tim Hunter T. Hunter	1,705	476	24	34	58	-1	0	0	1	0	4	0	321	7.5
22	Ken Daneyko K. Daneyko	1,689	777	26	86	112	+69	2	4	3	4	3	0	704	3.7
23	Stu Grimson S. Grimson	1,686	577	12	17	29	-39	1	0	0	0	2	0	166	7.2
24	Jeff Odgers J. Odgers	1,670	557	62	53	115	-85	15	9	0	0	3	0	538	11.5
25	Kelly Buchberger K. Buchberger	1,666	776	81	158	239	-98	5	4	12	16	24	1	806	10.0