Between the 1999-00 and 2008-09 seasons, the Detroit Red Wings had the most wins by a team, with 457 wins.

Interpreted as:

NHL most regular-season wins from 1999-00 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	457	738	177	50	54	1,018	.690	17	20	2,400	1,807	593	21.3	84.7	32.64	10.0	26.38	.907
2	Devils	415	738	223	51	49	930	.630	33	18	2,055	1,733	322	17.6	84.2	30.62	9.1	26.24	.911
3	Senators	402	738	232	47	57	908	.615	11	23	2,355	1,888	467	19.2	84.2	30.80	10.4	27.25	.906
4	Stars	398	738	231	59	50	905	.613	32	14	2,037	1,793	244	17.5	84.5	27.62	10.0	25.69	.905
5	Sharks	387	738	236	51	64	889	.602	15	20	2,111	1,845	266	18.3	83.9	28.89	9.9	27.32	.909
6	Avalanche	384	738	250	55	49	872	.591	24	17	2,163	1,921	242	18.9	83.0	29.01	10.1	27.88	.907
7	Canucks	371	738	252	56	59	857	.581	18	24	2,138	1,955	183	17.7	83.3	28.54	10.2	27.76	.905
8	Flyers	368	738	245	61	64	861	.583	12	24	2,132	1,939	193	17.9	83.5	29.88	9.7	27.99	.906
9	Maple Leafs	365	738	267	45	61	836	.566	16	25	2,185	2,115	70	18.2	81.6	28.90	10.2	28.44	.899
10	Sabres	365	738	277	44	52	826	.560	27	23	2,121	1,962	159	16.6	84.7	28.84	10.0	28.60	.907
11	Blues	346	738	270	53	69	814	.551	19	25	1,998	1,959	39	17.0	83.8	28.17	9.6	26.03	.898
12	Canadiens	342	738	290	44	62	790	.535	20	21	2,002	2,012	-10	18.5	83.0	27.78	9.8	30.57	.911
13	Hurricanes	340	738	289	60	49	789	.535	13	15	2,002	2,080	-78	16.3	82.7	29.80	9.1	28.00	.899
14	Bruins	338	738	263	59	78	813	.551	21	25	2,041	2,071	-30	16.8	82.6	30.23	9.1	29.17	.904
15	Flames	338	738	287	57	56	789	.535	11	17	1,943	2,000	-57	16.2	82.1	28.45	9.3	28.05	.903
16	Ducks	337	738	285	50	66	790	.535	22	27	1,907	1,915	-8	17.8	83.4	28.71	9.0	28.76	.910
17	Predators	336	738	295	53	54	779	.528	21	18	1,933	1,976	-43	15.6	84.4	27.64	9.5	29.57	.909
18	Capitals	333	738	295	51	59	776	.526	16	26	2,068	2,160	-92	18.4	81.5	28.60	9.8	30.12	.903
19	Oilers	333	738	278	63	64	793	.537	31	20	2,015	2,032	-17	15.6	83.3	27.68	9.9	28.15	.902
20	Rangers	328	738	308	38	64	758	.514	34	24	1,999	2,099	-100	16.6	82.3	30.22	9.0	29.41	.903
21	Penguins	318	738	316	39	65	740	.501	24	22	2,107	2,294	-187	18.3	81.2	27.33	10.4	30.71	.899
22	Kings	313	738	304	58	63	747	.506	20	18	2,013	2,119	-106	17.1	81.2	28.60	9.5	28.02	.898
23	Coyotes	310	738	317	63	48	731	.495	17	14	1,933	2,149	-216	15.7	81.6	27.58	9.5	29.99	.903
24	Islanders	297	738	345	46	50	690	.467	25	16	1,927	2,228	-301	15.8	82.1	28.78	9.1	30.39	.901
25	Blackhawks	296	738	323	55	64	711	.482	17	24	1,961	2,153	-192	14.9	83.0	28.29	9.4	28.52	.898