Between the 1999-00 and 2008-09 seasons, Donald Brashear had the most penalty minutes, with 1,415 minutes in the box.

Interpreted as:

most pims by a player 1999-00 to 2008-09

	NAME	PIM	GP	G	A	P	+/-	PPG	PPA	SHG	SHA	GWG	OTG	S	S%	FOW	FO	FOW%	HIT	BKS	TKA	GVA	TOI/GP
1	Donald Brashear D. Brashear	1,415	660	57	88	145	-27	2	8	0	0	8	0	710	8.0	26	83	31.3	1,146	135	209	284	10:48
2	Chris Neil C. Neil	1,298	511	61	73	134	+25	12	8	0	0	5	0	596	10.2	17	47	36.2	1,323	96	140	109	10:37
3	Matthew Barnaby M. Barnaby	1,280	499	64	106	170	+4	3	6	0	1	9	0	531	12.1	61	145	42.1	528	82	106	164	11:35
4	Jody Shelley J. Shelley	1,232	481	14	26	40	-34	1	2	0	0	2	0	292	4.8	4	22	18.2	614	65	32	54	6:06
5	Ian Laperriere I. Laperriere	1,183	681	82	133	215	-14	3	0	2	9	12	1	760	10.8	2,097	4,244	49.4	1,141	452	375	232	14:19
6	Sean Avery S. Avery	1,178	420	73	116	189	+18	7	25	4	2	12	0	876	8.3	639	1,258	50.8	640	93	119	195	13:24
7	Andre Roy A. Roy	1,157	502	35	31	66	-12	0	0	0	0	5	0	337	10.4	10	20	50.0	627	25	67	71	6:32
8	Peter Worrell P. Worrell	1,143	310	15	22	37	-44	2	3	0	0	2	0	280	5.4	4	31	12.9	778	45	39	53	8:32
9	Zdeno Chara Z. Chara	1,077	683	102	208	310	+71	53	84	4	16	17	3	1,427	7.1	11	29	37.9	2,113	868	295	600	25:02
10	Tie Domi T. Domi	1,057	462	54	64	118	-13	7	4	0	0	5	0	459	11.8	21	64	32.8	508	48	57	149	10:05
11	Wade Belak W. Belak	1,055	451	7	21	28	-34	0	0	0	0	0	0	190	3.7	0	2	0.0	570	154	33	114	7:38
12	Chris Simon C. Simon	1,018	543	101	99	200	+14	22	16	0	0	13	1	865	11.7	39	90	43.3	590	102	164	283	12:04
13	Brendan Witt B. Witt	1,007	638	15	76	91	-32	0	1	0	6	0	0	663	2.3	6	9	66.7	1,604	1,102	187	461	21:06
14	Todd Fedoruk T. Fedoruk	996	495	29	62	91	-15	2	2	0	0	2	0	327	8.9	7	36	19.4	516	59	56	112	8:15
15	Georges Laraque G. Laraque	982	617	49	96	145	+12	4	6	0	0	7	0	462	10.6	6	22	27.3	632	110	104	155	8:41
16	Bryan McCabe B. McCabe	965	671	104	257	361	+54	60	136	0	7	20	5	1,426	7.3	1	6	16.7	1,335	953	104	655	25:00
17	Eric Boulton E. Boulton	950	418	19	36	55	-18	0	0	0	0	1	0	299	6.4	6	21	28.6	334	66	60	66	6:23
18	Sean O'Donnell S. O'Donnell	944	713	17	115	132	+75	2	10	1	10	7	4	500	3.4	9	20	45.0	651	622	293	535	20:05
19	Brenden Morrow B. Morrow	943	591	173	216	389	+115	55	47	6	5	33	2	1,079	16.0	115	286	40.2	1,534	253	267	509	17:46
20	Darcy Tucker D. Tucker	931	644	170	199	369	-29	64	50	4	4	32	3	1,216	14.0	485	1,022	47.5	989	312	195	361	16:47
21	Eric Cairns E. Cairns	920	369	10	25	35	-36	0	0	0	3	1	0	184	5.4	0	1	0.0	508	246	61	173	12:37
22	Krzysztof Oliwa K. Oliwa	907	272	10	18	28	-23	1	1	0	0	2	0	161	6.2	4	12	33.3	192	15	32	47	5:24
23	Todd Bertuzzi T. Bertuzzi	905	613	206	307	513	+1	88	97	0	0	26	4	1,449	14.2	713	1,550	46.0	867	139	253	425	18:26
24	Bill Guerin B. Guerin	903	685	257	247	504	+12	76	95	2	1	44	7	2,212	11.6	94	212	44.3	767	227	277	509	18:27
25	Steve Staios S. Staios	887	630	46	120	166	-2	8	26	3	4	3	1	936	4.9	2	5	40.0	646	1,052	261	511	20:49