Between the 1933-34 and 1942-43 seasons, Charlie Conacher made the most game-winning goals, with 28 game-winners.

NHL most regular-season game-winning goals by a player 1933-34 to 1942-43

	NAME	GWG	GP	G	A	P	PIM	PPG	PPA	SHG	SHA	OTG
1	Charlie Conacher C. Conacher	28	300	125	118	243	267	19	35	1	0	2
2	Sweeney Schriner S. Schriner	27	411	166	184	350	123	23	42	4	2	6
3	Busher Jackson B. Jackson	24	422	145	152	297	196	25	22	0	5	3
4	Bill Cowley B. Cowley	22	387	115	236	351	97	16	17	0	0	1
5	Paul Thompson P. Thompson	20	269	97	112	209	131	25	31	1	2	2
6	Bill Thoms B. Thoms	20	475	123	185	308	147	13	25	1	4	3
7	Roy Conacher R. Conacher	19	162	92	51	143	40	8	3	0	1	3
8	Gordie Drillon G. Drillon	19	312	155	140	295	56	23	32	4	0	0
9	Herb Cain H. Cain	19	425	121	121	242	153	10	15	1	2	2
10	Lorne Carr L. Carr	19	441	142	153	295	114	23	30	4	2	4
11	Eddie Wiseman E. Wiseman	19	413	106	157	263	125	22	31	1	0	6
12	Bobby Bauer B. Bauer	18	229	81	101	182	30	7	4	0	2	2
13	Bryan Hextall Sr. B. Hextall Sr.	18	293	138	122	260	150	17	19	5	6	4
14	Neil Colville N. Colville	18	283	87	128	215	143	7	21	7	5	0
15	Cecil Dillon C. Dillon	18	332	116	103	219	63	23	21	10	1	5
16	Aurel Joliat A. Joliat	18	235	76	57	133	115	11	9	0	2	2
17	John Sorrell J. Sorrell	18	356	96	98	194	57	21	20	0	0	2
18	Nels Stewart N. Stewart	18	315	121	105	226	242	27	28	0	1	3
19	Marty Barry M. Barry	17	317	110	137	247	107	20	15	0	1	1
20	Buzz Boll B. Boll	17	398	114	105	219	184	19	14	4	1	2
21	Johnny Gottselig J. Gottselig	17	334	98	135	233	105	25	33	3	4	1
22	Flash Hollett F. Hollett	17	420	93	131	224	265	9	26	2	4	2
23	Woody Dumart W. Dumart	16	237	85	85	170	36	3	3	0	0	1
24	Larry Aurie L. Aurie	16	233	83	94	177	116	12	24	3	2	0
25	Dit Clapper D. Clapper	16	438	106	137	243	204	10	16	2	3	6