Cy Young has the most career losses when winning >2 games, with 316 games.

Interpreted as:

most regular-season losses by a pitcher with >2 wins

	NAME	W	L	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	ERA-	FIP	FIP-	H/9	PRAA
1	Cy Young C. Young	511	316	.382	.618	906	815	2.63	2,803	749	76	17	7356.0	7,092	2,147	3,167	138	1,217	161	84		29,565	156	3.43	1.49	2.30	0.17	9.5	4.1	1.13	.275	3.87	74	2.84	79	8.68	620
2	Pud Galvin P. Galvin	361	308	.460	.540	697	681	2.87	1,799	639	57	1	5941.1	6,352	1,895	3,315	121	744	54	18		25,160	220	2.73	1.13	2.42	0.18	7.2	3.0	1.19	.278	5.02	94	2.97	95	9.62	94.5
3	Nolan Ryan N. Ryan	324	292	.474	.526	807	773	3.19	5,714	222	61	3	5386.0	3,923	1,911	2,178	321	2,795	158	13	78	22,575	277	9.55	4.67	2.04	0.54	25.3	12.4	1.25	.265	3.64	90	2.96	83	6.56	370.2
4	Walter Johnson W. Johnson	417	279	.401	.599	802	666	2.17	3,509	531	110	34	5914.1	4,913	1,424	1,902	97	1,363	205	127		23,405	154	5.34	2.07	2.57	0.15	15.0	5.8	1.06	.264	2.89	68	2.42	76	7.48	472.8
5	Phil Niekro P. Niekro	318	274	.463	.537	864	716	3.35	3,342	245	45	29	5404.0	5,044	2,012	2,337	482	1,809	123	83	86	22,677	226	5.57	3.01	1.85	0.80	14.7	8.0	1.27	.270	3.89	87	3.61	95	8.40	116.1
6	Gaylord Perry G. Perry	314	265	.458	.542	777	690	3.11	3,534	303	53	10	5350.0	4,938	1,846	2,128	399	1,379	108	33	164	21,953	160	5.95	2.32	2.56	0.67	16.1	6.3	1.18	.275	3.58	85	3.06	85	8.31	312.9
7	Don Sutton D. Sutton	324	256	.441	.559	774	756	3.26	3,574	178	58	5	5282.1	4,692	1,914	2,104	472	1,343	82	12	102	21,631	112	6.09	2.29	2.66	0.80	16.5	6.2	1.14	.261	3.58	92	3.23	90	7.99	181.2
8	Jack Powell J. Powell	245	254	.509	.491	578	516	2.97	1,621	422	46	15	4389.0	4,319	1,450	1,991	110	1,021	120	57		17,896	67	3.32	2.09	1.59	0.23	9.1	5.7	1.22	.280	4.08	95	3.01	97	8.86	35
9	Eppa Rixey E. Rixey	266	251	.485	.515	692	554	3.15	1,350	290	37	14	4494.2	4,633	1,572	1,986	93	1,082	76	99		18,754	97	2.70	2.17	1.25	0.19	7.2	5.8	1.27	.281	3.98	88	3.29	91	9.28	162.7
10	Bert Blyleven B. Blyleven	287	250	.466	.534	692	685	3.31	3,701	242	60	0	4970.0	4,632	1,830	2,029	430	1,322	155	3	71	20,491	114	6.70	2.39	2.80	0.78	18.1	6.5	1.20	.282	3.67	85	3.18	82	8.39	368.6
11	Robin Roberts R. Roberts	286	245	.461	.539	676	609	3.41	2,357	305	45	25	4688.2	4,582	1,774	1,962	505	902	54	49	69	19,174	33	4.52	1.73	2.61	0.97	12.3	4.7	1.17	.265	3.77	89	3.50	91	8.80	179.6
12	Warren Spahn W. Spahn	363	245	.403	.597	750	665	3.09	2,583	382	63	28	5243.2	4,830	1,798	2,016	434	1,434	42	67	60	21,547	81	4.43	2.46	1.80	0.74	12.0	6.7	1.19	.258	3.46	84	3.44	94	8.29	124.4
13	Steve Carlton S. Carlton	329	244	.426	.574	741	709	3.22	4,136	254	55	2	5217.2	4,672	1,864	2,130	414	1,833	53	13	150	21,683	183	7.13	3.16	2.26	0.71	19.1	8.5	1.25	.279	3.67	87	3.14	86	8.06	271.5
14	Early Wynn E. Wynn	300	244	.449	.551	691	611	3.54	2,334	289	49	16	4564.0	4,291	1,796	2,037	338	1,775	64	67	36	19,408	51	4.60	3.50	1.31	0.67	12.0	9.1	1.33	.265	4.02	94	3.64	97	8.46	56.4
15	Jim Kaat J. Kaat	283	237	.456	.544	898	625	3.45	2,461	180	31	17	4530.1	4,620	1,738	2,038	395	1,083	122	102	116	19,023	128	4.89	2.15	2.27	0.78	12.9	5.7	1.26	.282	4.05	93	3.41	91	9.18	165.8
16	Frank Tanana F. Tanana	240	236	.496	.504	638	616	3.66	2,773	143	34	1	4188.1	4,063	1,704	1,910	448	1,255	129	10	116	17,641	119	5.96	2.70	2.21	0.96	15.7	7.1	1.27	.277	4.10	94	3.78	96	8.73	66.4
17	Gus Weyhing G. Weyhing	264	232	.468	.532	540	505	3.88	1,667	449	28	4	4337.0	4,576	1,872	2,796	120	1,570	277	34		19,188	240	3.46	3.26	1.06	0.25	8.7	8.2	1.42	.286	5.80	96	3.82	97	9.50	55.7
18	Tommy John T. John	288	231	.445	.555	760	700	3.34	2,245	162	46	3	4710.1	4,783	1,749	2,017	302	1,259	98	22	102	19,692	187	4.29	2.41	1.78	0.58	11.4	6.4	1.28	.284	3.85	90	3.37	89	9.14	208.3
19	Bob Friend B. Friend	197	230	.539	.461	602	497	3.58	1,734	163	36	10	3611.0	3,772	1,438	1,652	286	894	46	56	115	15,214	50	4.32	2.23	1.94	0.71	11.4	5.9	1.29	.284	4.12	94	3.35	89	9.40	172.2
20	Ted Lyons T. Lyons	260	230	.469	.531	594	484	3.67	1,073	356	27	25	4161.0	4,489	1,696	2,056	222	1,121	31	91		17,797	55	2.32	2.42	0.96	0.48	6.0	6.3	1.35	.278	4.45	85	4.01	95	9.71	91.7
21	Greg Maddux G. Maddux	355	227	.390	.610	744	740	3.16	3,371	109	35	0	5008.1	4,726	1,756	1,981	353	999	137	3	177	20,421	70	6.06	1.80	3.37	0.63	16.5	4.9	1.14	.281	3.56	76	3.25	78	8.49	519.5
22	Fergie Jenkins F. Jenkins	284	226	.443	.557	664	594	3.34	3,192	267	49	7	4500.2	4,142	1,669	1,853	484	997	84	37	116	18,400	62	6.38	1.99	3.20	0.97	17.3	5.4	1.14	.268	3.71	87	3.27	88	8.28	222.9
23	Red Ruffing R. Ruffing	273	225	.452	.548	624	538	3.80	1,987	335	45	18	4344.0	4,284	1,833	2,115	254	1,541	58	69		18,546	46	4.12	3.19	1.29	0.53	10.7	8.3	1.34	.274	4.38	91	3.93	95	8.88	82.3
24	Tim Keefe T. Keefe	342	225	.397	.603	600	594	2.63	2,564	554	39	2	5049.2	4,438	1,474	2,470	75	1,233	83	7		20,941	240	4.57	2.20	2.08	0.13	12.2	5.9	1.12	.257	4.40	79	2.92	87	7.91	239.2
25	Bobo Newsom B. Newsom	211	222	.513	.487	600	483	3.98	2,082	246	31	21	3759.1	3,769	1,664	1,908	206	1,732	61	71		16,467	60	4.98	4.15	1.20	0.49	12.6	10.5	1.46	.288	4.57	95	3.81	92	9.02	144.5