what teams have won the world series with a losing record against winning teams

The Pittsburgh Pirates have a record of 23-24 in the World Series all-time.

	TEAM	REC	SERIES W	W	L	SERIES	W%	L%	G	AB	R	H	2B	3B	HR	RBI	BB	HBP	SO	SB	CS	PA	TB	XBH	SH	SF	IBB	GIDP	AVG	OBP	SLG	OPS
1	Pirates	23-24	5	23	24	World Series	.489	.511	47	1,576	175	401	76	16	19	161	109	19	226	41	16	1,738	566	111	29	5	12	24	.254	.310	.359	.669
2	Red Sox	49-29	9	49	29	World Series	.628	.372	79	2,653	312	644	105	42	50	290	260	21	458	23	27	3,001	983	197	55	12	35	43	.243	.314	.371	.685
3	Giants	57-57	8	57	57	World Series	.500	.500	116	3,865	426	959	142	29	64	393	314	24	638	63	61	4,276	1,351	235	62	11	29	66	.248	.308	.350	.657
4	Athletics	41-34	9	41	34	World Series	.547	.453	75	2,457	267	559	107	14	46	245	223	13	461	41	32	2,753	832	167	56	4	22	31	.228	.295	.339	.633
5	Cubs	23-36	3	23	36	World Series	.390	.610	60	1,997	205	487	85	17	21	179	162	12	366	61	43	2,232	669	123	59	2	7	29	.244	.304	.335	.639
6	White Sox	17-13	3	17	13	World Series	.567	.433	30	1,000	106	246	45	8	12	93	79	11	156	24	23	1,111	343	65	20	1	4	15	.246	.308	.343	.651
7	Tigers	27-37	4	27	37	World Series	.422	.578	65	2,164	227	491	84	11	33	213	225	22	351	34	27	2,448	696	128	34	3	20	37	.227	.306	.322	.627
8	Braves	28-31	4	28	31	World Series	.475	.525	59	1,961	213	462	76	10	51	206	207	10	377	42	17	2,225	711	137	34	13	17	46	.236	.310	.363	.672
9	Phillies	16-27	2	16	27	World Series	.372	.628	43	1,400	156	320	61	6	43	149	148	12	304	29	13	1,585	522	110	16	9	13	28	.229	.306	.373	.679
10	Dodgers	57-71	8	57	71	World Series	.445	.555	128	4,201	454	959	152	27	114	428	403	29	800	66	50	4,709	1,507	293	57	19	34	77	.228	.299	.359	.658
11	Reds	26-25	5	26	25	World Series	.510	.490	51	1,690	192	411	77	18	27	186	148	13	225	40	26	1,887	605	122	27	9	22	31	.243	.308	.358	.666
12	Indians	17-20	2	17	20	World Series	.459	.541	37	1,219	137	279	50	5	28	125	138	7	227	21	14	1,384	423	83	16	4	14	23	.229	.310	.347	.657
13	Yankees	135-94	27	135	94	World Series	.590	.410	230	7,713	1,013	1,919	283	52	225	958	814	58	1,342	87	59	8,702	2,981	560	94	23	87	151	.249	.324	.386	.711
14	Twins	19-21	3	19	21	World Series	.475	.525	40	1,340	145	319	46	9	36	143	128	6	229	23	18	1,497	491	91	21	2	15	21	.238	.307	.366	.673
15	Cardinals	58-60	11	58	60	World Series	.492	.508	118	3,931	430	943	185	27	58	395	315	15	659	67	35	4,344	1,356	270	72	11	48	55	.240	.298	.345	.643
16	Orioles	21-18	3	21	18	World Series	.538	.462	39	1,261	135	267	41	4	33	122	125	6	240	5	5	1,407	415	78	8	7	15	27	.212	.284	.329	.614
17	Mets	13-16	2	13	16	World Series	.448	.552	29	1,016	106	241	30	2	27	91	87	10	208	9	6	1,138	356	59	17	8	13	18	.237	.302	.350	.652
18	Royals	13-12	2	13	12	World Series	.520	.480	25	869	105	232	48	5	15	100	82	4	185	21	6	970	335	68	8	7	11	26	.267	.331	.386	.716
19	Brewers	3-4	0	3	4	World Series	.429	.571	7	238	33	64	12	2	5	29	19	1	28	1	2	260	95	19	1	1	3	7	.269	.324	.399	.723
20	Padres	1-8	0	1	8	World Series	.111	.889	9	300	28	76	14	1	6	25	23	0	55	3	5	329	110	21	1	5	0	4	.253	.302	.367	.668
21	Blue Jays	8-4	2	8	4	World Series	.667	.333	12	402	62	109	21	5	12	62	43	4	63	13	4	459	176	38	2	8	4	9	.271	.341	.438	.779
22	Marlins	8-5	2	8	5	World Series	.615	.385	13	453	54	115	20	1	10	51	50	2	96	6	3	515	167	31	6	4	5	11	.254	.328	.369	.697
23	Diamondbacks	5-7	1	5	7	World Series	.417	.583	12	420	59	112	24	1	9	58	33	6	111	9	3	473	165	34	10	4	7	9	.267	.326	.393	.719
24	Angels	4-3	1	4	3	World Series	.571	.429	7	245	41	76	15	1	7	38	23	2	38	6	0	275	114	23	2	3	5	6	.310	.370	.465	.835
25	Astros	13-17	2	13	17	World Series	.433	.567	30	1,038	120	246	50	2	36	116	100	14	253	22	4	1,165	408	88	7	6	15	23	.237	.311	.393	.704