4 players were tied for the oldest in 1999-00. They were 39 years old. The first three are Ray Bourque, Guy Carbonneau and Igor Larionov.

	NAME	AGE	SEASON	TM	GP	G	A	P	+/-	PIM	PPG	PPA	SHG	SHA	GWG	OTG	S	S%	FOW	FO	FOW%	HIT	BKS	TKA	GVA	TOI/GP
1	Ray Bourque R. Bourque	39	1999-00	TOT	79	18	34	52	-2	26	13	24	0	0	0	0	260	6.9	0	1	0.0	164	94	65	72	27:11
2	Guy Carbonneau G. Carbonneau	39	1999-00	DAL	69	10	6	16	+10	36	0	0	1	0	4	0	70	14.3	686	1,290	53.2	135	65	38	34	15:38
3	Igor Larionov I. Larionov	39	1999-00	DET	79	9	38	47	+13	28	3	12	0	0	4	0	69	13.0	318	729	43.6	22	18	24	58	16:05
4	Mark Messier M. Messier	39	1999-00	VAN	66	17	37	54	-15	30	6	13	0	1	4	2	131	13.0	956	1,684	56.8	50	26	43	69	21:12
5	Chris Chelios C. Chelios	38	1999-00	DET	81	3	31	34	+48	103	0	4	0	2	0	0	135	2.2	0	0		120	86	47	113	25:16
6	Paul Coffey P. Coffey	38	1999-00	CAR	69	11	29	40	-6	40	6	16	0	0	3	0	155	7.1	0	0		18	70	21	84	22:35
7	Grant Ledyard G. Ledyard	38	1999-00	OTT	40	2	4	6	-3	8	0	0	0	0	1	0	42	4.8	0	0		58	31	7	24	14:45
8	Larry Murphy L. Murphy	38	1999-00	DET	81	10	30	40	+4	45	7	9	0	0	0	0	146	6.8	1	1	100.0	38	92	23	81	21:50
9	Geoff Courtnall G. Courtnall	37	1999-00	STL	6	2	2	4	+3	6	0	1	0	0	1	0	15	13.3	0	0		7	2	0	9	14:20
10	Grant Fuhr G. Fuhr	37	1999-00	CGY	23	0	0	0		2																52:23
11	Glenn Healy G. Healy	37	1999-00	TOR	20	0	1	1		2																58:11
12	Adam Oates A. Oates	37	1999-00	WSH	82	15	56	71	+13	14	5	16	0	0	6	2	93	16.1	1,235	2,176	56.8	19	45	49	121	22:20
13	Greg Adams G. Adams	36	1999-00	PHX	69	19	27	46	-1	14	5	7	0	0	0	0	129	14.7	64	141	45.4	27	15	41	47	16:58
14	Dave Andreychuk D. Andreychuk	36	1999-00	TOT	77	20	16	36	-20	30	8	8	0	0	3	0	233	8.6	241	461	52.3	78	75	72	36	19:22
15	Kevin Dineen K. Dineen	36	1999-00	OTT	67	4	8	12	+2	57	0	0	0	0	1	0	71	5.6	5	10	50.0	67	14	11	12	9:31
16	Mike Eagles M. Eagles	36	1999-00	WSH	25	2	0	2	-7	15	0	0	0	0	1	0	13	15.4	58	115	50.4	41	14	5	2	7:37
17	Ron Francis R. Francis	36	1999-00	CAR	78	23	50	73	+10	18	7	22	0	0	4	0	150	15.3	835	1,566	53.3	48	53	45	36	21:58
18	Garry Galley G. Galley	36	1999-00	LAK	70	9	21	30	+9	52	2	11	0	0	1	0	96	9.4	0	0		152	79	26	80	20:15
19	Doug Gilmour D. Gilmour	36	1999-00	TOT	74	25	48	73	-9	63	10	13	0	0	3	2	113	22.1	523	976	53.6	42	37	28	54	19:50
20	Al MacInnis A. MacInnis	36	1999-00	STL	61	11	28	39	+20	34	6	13	0	1	7	1	245	4.5	0	0		44	72	41	79	26:07
21	Marty McSorley M. McSorley	36	1999-00	BOS	27	2	3	5	+2	62	0	1	0	0	0	0	24	8.3	0	0		35	11	4	10	14:01
22	Sergei Nemchinov S. Nemchinov	36	1999-00	NJD	53	10	16	26	+1	18	0	2	1	1	1	0	55	18.2	207	453	45.7	47	19	41	23	13:42
23	James Patrick J. Patrick	36	1999-00	BUF	66	5	8	13	+8	22	0	0	0	0	3	0	40	12.5	0	0		44	61	19	33	15:59
24	Brian Skrudland B. Skrudland	36	1999-00	DAL	22	1	2	3	0	22	0	0	0	0	0	0	16	6.3	113	195	57.9	20	8	1	6	8:24
25	Steve Smith S. Smith	36	1999-00	CGY	20	0	4	4	-13	42	0	0	0	0	0	0	10	0.0	0	0		39	33	5	18	21:07