Between the 1998-99 and 2008-09 seasons, the Detroit Red Wings had the most wins by a team, with 500 wins.

Interpreted as:

NHL most regular-season wins from 1998-99 to 2008-09

	TEAM	W	GP	L	T	OTL	PTS	PTS%	SOW	SOL	G	GA	DIFF	PP%	PK%	S/GP	S%	SA/GP	SV%
1	Red Wings	500	820	209	57	54	1,111	.677	17	20	2,645	2,009	636	20.7	85.0	32.57	9.9	26.44	.907
2	Devils	462	820	247	62	49	1,035	.631	33	18	2,303	1,929	374	17.8	84.4	30.68	9.2	26.09	.910
3	Stars	449	820	250	71	50	1,019	.621	32	14	2,273	1,961	312	17.6	84.7	27.62	10.0	25.52	.906
4	Senators	446	820	255	62	57	1,011	.616	11	23	2,594	2,067	527	18.7	84.4	30.77	10.3	27.05	.907
5	Avalanche	428	820	278	65	49	970	.591	24	17	2,402	2,126	276	18.9	83.1	28.91	10.1	27.87	.907
6	Sharks	418	820	269	69	64	969	.591	15	20	2,307	2,036	271	17.8	84.0	28.62	9.8	27.29	.909
7	Maple Leafs	410	820	297	52	61	933	.569	16	25	2,453	2,346	107	17.8	81.5	28.84	10.4	28.47	.900
8	Flyers	405	820	271	80	64	954	.582	12	24	2,363	2,135	228	17.7	83.6	29.88	9.6	27.48	.905
9	Sabres	402	820	305	61	52	917	.559	27	23	2,328	2,137	191	16.3	84.9	28.58	9.9	28.74	.909
10	Canucks	394	820	299	68	59	915	.558	18	24	2,330	2,213	117	17.5	83.2	28.06	10.1	27.92	.903
11	Blues	383	820	302	66	69	901	.549	19	25	2,235	2,168	67	17.2	84.2	28.37	9.6	25.71	.897
12	Bruins	377	820	293	72	78	904	.551	21	25	2,255	2,252	3	16.9	83.1	29.96	9.2	28.97	.905
13	Canadiens	374	820	329	55	62	865	.527	20	21	2,186	2,221	-35	18.1	83.4	27.77	9.6	30.20	.910
14	Hurricanes	374	820	319	78	49	875	.534	13	15	2,212	2,282	-70	15.8	82.9	29.43	9.2	28.12	.901
15	Ducks	372	820	319	63	66	873	.532	22	27	2,122	2,121	1	18.2	83.5	28.68	9.0	29.05	.911
16	Flames	368	820	327	69	56	861	.525	11	17	2,154	2,234	-80	16.0	81.9	28.46	9.2	28.19	.903
17	Oilers	366	820	315	75	64	871	.531	31	20	2,245	2,258	-13	15.4	83.2	27.84	9.8	28.05	.902
18	Capitals	364	820	340	57	59	844	.515	16	26	2,268	2,378	-110	18.3	81.8	28.64	9.7	29.72	.902
19	Predators	364	820	342	60	54	842	.513	21	18	2,123	2,237	-114	15.3	83.8	27.58	9.4	29.91	.909
20	Rangers	361	820	346	49	64	835	.509	34	24	2,216	2,326	-110	16.9	82.6	29.74	9.1	29.49	.904
21	Penguins	356	820	346	53	65	830	.506	24	22	2,349	2,519	-170	18.3	81.2	27.14	10.6	30.23	.898
22	Coyotes	349	820	348	75	48	821	.501	17	14	2,138	2,346	-208	15.4	82.1	27.75	9.4	29.74	.904
23	Kings	345	820	349	63	63	816	.498	20	18	2,202	2,341	-139	16.7	81.6	28.57	9.4	28.21	.899
24	Blackhawks	325	820	364	67	64	781	.476	17	24	2,163	2,401	-238	14.9	82.7	28.08	9.4	28.60	.898
25	Islanders	321	820	393	56	50	748	.456	25	16	2,121	2,472	-351	15.8	82.2	28.53	9.1	30.19	.900