Christy Mathewson has the most career wins versus the Pirates, with 54 wins.

Interpreted as:

pitchers with most regular-season wins vs pirates

	NAME	W	L	W%	G	GS	ERA	SO	CG	SHO	SV	IP	H	ER	R	HR	BB	HBP	GF	IBB	TBF	WP	K/9	BB/9	K/BB	HR/9	K%	BB%	WHIP	BABIP	RA	H/9
1	Christy Mathewson C. Mathewson	54	38	.587	107	89	1.04	378	63	8	6	770.0	712		296	17	125	11	17			22	4.42	1.46	3.02	0.20		4.1	1.09	.277	3.46	8.32
2	Warren Spahn W. Spahn	49	34	.590	104	95	3.33	382	49	9	5	718.0	681	266	302	50	217	4	8		2,991	9	4.79	2.72	1.76	0.63	12.8	7.3	1.25	.270	3.79	8.54
3	Carl Hubbell C. Hubbell	49	21	.700	83	73	3.03	215	48	5	3	579.2	585	195	229	26	120	8	9		2,424	9	3.34	1.86	1.79	0.40	8.9	5.0	1.22	.272	3.56	9.08
4	Grover Alexander G. Alexander	44	32	.579	89	81	2.55	286	56	7	1	678.2	657		274	19	109	11	7			1	3.79	1.45	2.62	0.25		4.0	1.13	.275	3.63	8.71
5	Robin Roberts R. Roberts	40	25	.615	79	67	3.61	270	40	8	6	528.1	519	212	232	51	97	5	11		2,166	4	4.60	1.65	2.78	0.87	12.5	4.5	1.17	.269	3.95	8.84
6	Steve Carlton S. Carlton	39	25	.609	78	77	3.26	449	30	6	0	574.2	522	208	241	46	170	9	0	16	2,377	30	7.03	2.66	2.64	0.72	18.9	7.2	1.20	.280	3.77	8.18
7	Freddie Fitzsimmons F. Fitzsimmons	37	24	.607	87	73	3.27	129	35	5	1	596.2	600	217	259	26	162	9	10		2,520	7	1.95	2.44	0.80	0.39	5.1	6.4	1.28	.262	3.91	9.05
8	Eppa Rixey E. Rixey	36	53	.404	113	96	3.04	202	44	7	0	741.0	801		338	11	158	15	10			21	2.45	1.92	1.28	0.13		5.0	1.29	.286	4.11	9.73
9	Bucky Walters B. Walters	34	24	.586	68	64	2.73	189	42	8	0	497.0	453	151	183	17	185	8	2		2,076	10	3.42	3.35	1.02	0.31	9.1	8.9	1.28	.260	3.31	8.20
10	Curt Simmons C. Simmons	32	18	.640	64	60	2.99	209	22	7	0	424.0	436	141	187	21	117	3	3		1,817	2	4.44	2.48	1.79	0.45	11.5	6.4	1.30	.283	3.97	9.25
11	Art Nehf A. Nehf	32	22	.593	73	53	2.55	145	33	8	3	469.2	446		159	12	100	5	18			5	2.78	1.92	1.45	0.23		5.3	1.16	.266	3.05	8.55
12	Rube Marquard R. Marquard	32	24	.571	75	57	2.43	233	33	5	1	488.0	441		185	17	129	7	10		1,985	9	4.30	2.38	1.81	0.31	11.7	6.5	1.17	.265	3.41	8.13
13	Burleigh Grimes B. Grimes	31	30	.508	77	67	3.91	168	42	6	0	540.2	579	235	283	13	171	12	7		2,343	11	2.80	2.85	0.98	0.22	7.2	7.3	1.39	.286	4.71	9.64
14	Jesse Haines J. Haines	30	28	.517	84	60	3.86	128	35	1	0	512.2	534	220	250	12	139	9	14		2,164	11	2.25	2.44	0.92	0.21	5.9	6.4	1.31	.278	4.39	9.37
15	Hal Schumacher H. Schumacher	29	11	.725	58	44	2.79	123	22	4	2	364.1	320	113	136	14	119	3	8		1,504	9	3.04	2.94	1.03	0.35	8.2	7.9	1.20	.246	3.36	7.90
16	Paul Derringer P. Derringer	29	26	.527	73	56	3.79	171	30	6	3	451.2	532	190	223	7	97	1	14		1,955	2	3.41	1.93	1.76	0.14	8.7	5.0	1.39	.313	4.44	10.60
17	Bill Doak B. Doak	29	17	.630	73	61	2.53	146	28	8	2	445.1	407	125	157	8	145	9	9		1,849	1	2.95	2.93	1.01	0.16	7.9	7.8	1.24	.259	3.17	8.23
18	Juan Marichal J. Marichal	27	12	.692	45	44	2.81	212	30	6	0	339.1	307	106	131	24	67	2	1	12	1,368	4	5.62	1.78	3.16	0.64	15.5	4.9	1.10	.266	3.47	8.14
19	Bob Gibson B. Gibson	27	16	.628	57	53	2.68	357	26	6	0	430.0	387	128	151	27	125	8	2	15	1,775	12	7.47	2.62	2.86	0.57	20.1	7.0	1.19	.286	3.16	8.10
20	Joe Nuxhall J. Nuxhall	27	14	.659	66	44	3.82	171	13	5	0	351.0	355	149	157	29	93	8	4		1,465	7	4.38	2.38	1.84	0.74	11.7	6.3	1.28	.280	4.03	9.10
21	Lew Burdette L. Burdette	27	11	.711	68	48	3.24	128	22	5	5	402.2	438	145	159	23	53	6	11		1,644	5	2.86	1.18	2.42	0.51	7.8	3.2	1.22	.289	3.55	9.79
22	Herm Wehmeier H. Wehmeier	27	11	.711	58	45	4.07	164	19	3	1	347.1	333	157	171	28	166	3	3		1,496	6	4.25	4.30	0.99	0.73	11.0	11.1	1.44	.269	4.43	8.63
23	Greg Maddux G. Maddux	26	17	.605	53	53	2.64	257	7	5	0	368.0	338	108	124	24	94	10	0	15	1,509	5	6.29	2.30	2.73	0.59	17.0	6.2	1.17	.279	3.03	8.27
24	Don Sutton D. Sutton	26	19	.578	58	58	2.70	302	16	3	0	423.2	361	127	142	33	83	7	0	10	1,680	13	6.42	1.76	3.64	0.70	18.0	4.9	1.05	.261	3.02	7.67
25	Phil Niekro P. Niekro	26	21	.553	72	54	3.52	290	24	6	1	439.1	410	172	199	39	116	9	10	17	1,823	23	5.94	2.38	2.50	0.80	15.9	6.4	1.20	.271	4.08	8.40