Patrick Roy has won the most career Conn Smythe Trophies in the playoffs, with 3.

Interpreted as:

most conn smith trophies by a player

	NAME	SMYTHE	GP	G	A	P	+/-	PIM	PPG	PPA	SHG	SHA	GWG	OTG	S	S%	FOW	FO	FOW%	HIT	BKS	TKA	GVA	TOI/GP
1	Patrick Roy P. Roy	3	247	0	11	11		54																61:34
2	Sidney Crosby S. Crosby	2	180	71	130	201	+18	83	20	55	0	0	9	1	542	13.1	2,127	4,116	51.7	185	87	133	158	20:56
3	Mario Lemieux M. Lemieux	2	107	76	96	172	+20	87	29	49	7	1	11	0	402	18.9	167	360	46.4	10	6	20	23	24:35
4	Wayne Gretzky W. Gretzky	2	208	122	260	382	+91	66	35	90	12	17	24	4	699	17.5
5	Bobby Orr B. Orr	2	74	26	66	92	+60	107	8	24	3	7	7	1	358	7.3
6	Bernie Parent B. Parent	2	71	0	0	0		4																60:21
7	Cale Makar C. Makar	1	79	22	63	85	+23	20	9	25	1	1	5	1	226	9.7	0	0		100	122	78	64	24:43
8	Connor McDavid C. McDavid	1	96	44	106	150	+31	28	13	41	2	1	5	2	330	13.3	517	1,126	45.9	180	62	84	89	23:38
9	Sam Bennett S. Bennett	1	107	40	38	78	+11	178	10	11	0	0	3	0	298	13.4	370	878	42.1	445	51	40	74	17:04
10	Jonathan Marchessault J. Marchessault	1	102	36	40	76	+37	66	8	9	0	0	6	0	335	10.7	77	205	37.6	282	31	53	61	17:13
11	Andrei Vasilevskiy A. Vasilevskiy	1	120	0	1	1	0	4	0	0	0	0	0	0	0		0	0		1	0	18	56	60:31
12	Victor Hedman V. Hedman	1	170	23	97	120	+18	94	10	43	0	1	5	1	425	5.4	0	0		228	323	79	176	24:58
13	Ryan O'Reilly R. O'Reilly	1	81	26	41	67	0	15	10	10	0	3	5	1	174	14.9	886	1,684	52.6	50	61	68	33	21:06
14	Jonathan Quick J. Quick	1	93	0	1	1	0	18	0	0	0	0	0	0	0		0	0		0	0	0	14	60:35
15	Patrick Kane P. Kane	1	143	53	85	138	+4	70	8	36	1	0	11	5	445	11.9	16	62	25.8	49	34	81	87	20:21
16	Duncan Keith D. Keith	1	151	19	72	91	+20	70	2	27	0	2	5	1	323	5.9	0	0		120	264	86	181	27:07
17	Jonathan Toews J. Toews	1	137	45	74	119	+12	84	19	28	3	2	11	2	350	12.9	1,691	2,985	56.6	170	70	116	51	20:38
18	Alex Ovechkin A. Ovechkin	1	161	77	70	147	+3	83	31	33	0	0	11	1	675	11.4	11	15	73.3	672	87	72	136	20:56
19	Tim Thomas T. Thomas	1	51	0	1	1		4																61:04
20	Evgeni Malkin E. Malkin	1	177	67	113	180	+6	242	28	53	1	1	13	2	608	11.0	816	1,753	46.5	200	93	136	181	19:51
21	Cam Ward C. Ward	1	41	0	1	1		0																59:03
22	Jean-Sebastien Giguere J. Giguere	1	52	0	2	2		0																60:54
23	Brad Richards B. Richards	1	146	37	68	105	-13	65	15	27	0	1	9	1	449	8.2	1,039	2,186	47.5	87	73	69	91	19:58
24	Henrik Zetterberg H. Zetterberg	1	137	57	63	120	+41	79	21	27	2	3	8	1	514	11.1	951	1,836	51.8	150	63	91	86	21:03
25	Justin Williams J. Williams	1	162	41	61	102	+30	152	6	15	1	1	8	2	429	9.6	38	84	45.2	158	78	85	127	17:45