Warren Spahn has the most career wins against the Cubs, with 48 wins.

Interpreted as:

most regular-season wins for player vs cubs

	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	Warren Spahn W. Spahn	48	19	.716	87	74	2.85	342	44	10	4	580.1	529	184	207	50	123	3	10	2	2,344	7	5.30	1.91	2.78	0.78	14.6	5.2	1.12	.262	3.21	8.20
2	Christy Mathewson C. Mathewson	46	39	.541	96	87	0.89	355	75	14	5	749.1	654		283	18	113	4	8			17	4.26	1.36	3.14	0.22		3.8	1.02	.257	3.40	7.85
3	Burleigh Grimes B. Grimes	43	26	.623	83	68	3.30	217	46	7	3	600.0	637		272	18	210	14	12		2,585	9	3.26	3.15	1.03	0.27	8.4	8.1	1.41	.291	4.08	9.56
4	Steve Carlton S. Carlton	41	20	.672	77	72	3.11	421	29	7	0	533.0	487	184	212	49	156	10	2	16	2,207	16	7.11	2.63	2.70	0.83	19.1	7.1	1.21	.279	3.58	8.22
5	Paul Derringer P. Derringer	38	24	.613	81	65	2.63	268	41	5	1	561.1	515	164	197	28	110	4	10		2,288	10	4.30	1.76	2.44	0.45	11.7	4.8	1.11	.259	3.16	8.26
6	Eppa Rixey E. Rixey	37	36	.507	98	82	3.24	201	45	7	1	649.0	639		295	16	200	13	13			16	2.79	2.77	1.00	0.22		7.4	1.29	.273	4.09	8.86
7	Robin Roberts R. Roberts	36	24	.600	73	64	2.98	284	39	8	3	521.2	475	173	188	50	90	13	7		2,096	2	4.90	1.55	3.16	0.86	13.5	4.3	1.08	.256	3.24	8.19
8	Rip Sewell R. Sewell	36	19	.655	75	54	2.84	140	33	6	6	446.2	430	141	169	15	130	4	18		1,886	6	2.82	2.62	1.08	0.30	7.4	6.9	1.25	.260	3.41	8.66
9	Dazzy Vance D. Vance	34	21	.618	71	55	3.28	383	32	4	2	467.0	430	170	192	27	130	7	9		1,924	4	7.38	2.51	2.95	0.52	19.9	6.8	1.20	.293	3.70	8.29
10	Carl Hubbell C. Hubbell	33	27	.550	84	68	3.20	274	33	4	3	542.2	550	193	224	42	117	11	12		2,262	9	4.54	1.94	2.34	0.70	12.1	5.2	1.23	.279	3.71	9.12
11	Slim Sallee S. Sallee	32	28	.533	81	60	1.78	184	38	3	4	532.1	477		194	10	105	8	14		2,125	1	3.11	1.78	1.75	0.17	8.7	4.9	1.09	.257	3.28	8.06
12	Harry Brecheen H. Brecheen	31	12	.721	61	47	2.03	202	35	11	2	420.1	337	95	102	22	99	6	5		1,656	3	4.33	2.12	2.04	0.47	12.2	6.0	1.04	.237	2.18	7.22
13	Don Drysdale D. Drysdale	30	19	.612	69	60	2.67	376	27	7	2	465.2	400	138	161	35	115	23	7	17	1,892	15	7.27	2.22	3.27	0.68	19.9	6.1	1.11	.272	3.11	7.73
14	Wilbur Cooper W. Cooper	30	27	.526	79	58	2.60	217	38	7	4	509.2	489	147	194	8	123	11	17		2,091	6	3.83	2.17	1.76	0.14	10.4	5.9	1.20	.278	3.43	8.64
15	Grover Alexander G. Alexander	30	23	.566	64	58	2.62	234	38	10	1	457.1	395		172	26	105	7	3			3	4.60	2.07	2.23	0.51		5.7	1.09	.251	3.38	7.77
16	Dwight Gooden D. Gooden	28	4	.875	40	39	3.32	235	11	3	1	284.1	264	105	116	18	90	7	1	3	1,190	5	7.44	2.85	2.61	0.57	19.7	7.6	1.25	.293	3.67	8.36
17	Bob Gibson B. Gibson	28	22	.560	58	53	2.95	338	33	11	1	440.0	367	144	154	27	161	6	2	24	1,823	13	6.91	3.29	2.10	0.55	18.5	8.8	1.20	.263	3.15	7.51
18	Ken Raffensberger K. Raffensberger	28	17	.622	62	46	2.28	142	30	10	3	382.1	353	97	119	14	54	4	9		1,522	1	3.34	1.27	2.63	0.33	9.3	3.5	1.06	.259	2.80	8.31
19	Phil Niekro P. Niekro	27	17	.614	62	52	3.19	241	24	5	2	395.1	375	140	168	38	97	17	7	11	1,641	14	5.49	2.21	2.48	0.87	14.7	5.9	1.19	.270	3.82	8.54
20	Bob Friend B. Friend	27	22	.551	72	59	3.52	247	22	5	2	449.2	442	176	194	30	101	5	6	19	1,861	8	4.94	2.02	2.45	0.60	13.3	5.4	1.21	.279	3.88	8.85
21	Art Nehf A. Nehf	26	22	.542	61	46	3.23	120	23	5	3	354.1	333		155	11	99	4	12			12	3.05	2.51	1.21	0.28		6.8	1.22	.263	3.94	8.46
22	Lew Burdette L. Burdette	25	17	.595	67	48	3.70	138	19	3	4	376.2	395	155	182	45	56	7	10		1,552	1	3.30	1.34	2.46	1.08	8.9	3.6	1.20	.268	4.35	9.44
23	Curt Simmons C. Simmons	25	19	.568	68	59	3.46	261	20	5	1	429.0	420	165	195	41	143	7	5		1,825	11	5.48	3.00	1.83	0.86	14.3	7.8	1.31	.276	4.09	8.81
24	Harry Gumbert H. Gumbert	25	20	.556	79	41	3.92	122	18	1	5	344.0	351	150	168	12	140	6	23		1,505	3	3.19	3.66	0.87	0.31	8.1	9.3	1.43	.277	4.40	9.18
25	Rube Marquard R. Marquard	25	27	.481	74	61	2.66	229	24	4	2	453.2	458		214	14	138	6	9		1,915	14	4.54	2.74	1.66	0.28	12.0	7.2	1.31	.291	4.25	9.09