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Simple Summary: Diarrhea often occurs in suckling piglets and milk secreted by lactating sows with metritis–vaginitis–mastitis is one of the most important contributors. Chinese herbal medicine has antibacterial and anti-inflammatory effects due to its bioactive ingredients, and it is of interest to explore whether maternal feeding with Chinese herbal medicine can increase the level of milk ingredients with anti-infectious and anti-inflammatory properties. The present study found that supplementation of fermented compound Chinese medicine feed additive to sows increased the concentration of functional ingredients, such as quercetin, pinocembrin, chlorogenic acid, methyl succinic acid, L-tryptophan, adenosine, guanine, arteannuin, inosine, guanosine, benzene-1,2,4-triol, hypoxanthine, adenine, ferulic acid, echimidine N-oxide, pogostone, kynurenine and trehalose 6-phosphate in the milk of sows, most of these functional ingredients have anti-infectious, anti-inflammatory, anti-oxidative and immune-enhancing effects. The findings of this study hint that supplementation with fermented compound Chinese medicine feed additive in sows is beneficial for the improvement of milk quality. Different untargeted metabolomics approaches were used to identify the differential metabolites between milk samples collected from two groups. Sows were supplemented with fermented compound Chinese medicine feed additive at levels of 0 g/d/sow (control group, n = 10) and 50 g/d/sow (experimental group, n = 10), respectively, from d 104 of gestation to d 25 of lactation, samples of colostrum and mature milk were collected. Data indicated that supplementing fermented compound Chinese medicine feed additive to sows significantly increased the concentrations of quercetin, pinocembrin, chlorogenic acid, methyl succinic acid, L-tryptophan, adenosine, guanine, arteannuin, ferulic acid, echimidine N-oxide, pogostone and kynurenine in the colostrum and inosine, guanosine, benzene-1,2,4-triol, hypoxanthine, adenine, trehalose 6-phosphate in mature milk, respectively. Seven pathways (flavone and flavanol biosynthesis, galactose metabolism, phenylpropanoid biosynthesis, stilbenoid and gingerol biosynthesis, flavonoid biosynthesis, ABC transporters and purine metabolism) in colostrum and two pathways (sucrose metabolism and retrograde endocannabinoid signaling) in mature milk were significantly enriched in the experimental group compared to control group, respectively. The supplementation of fermented compound Chinese medicine feed additive to sows increased the level of antibacterial and anti-inflammatory ingredients in milk and the findings of this study hint that supplementation with fermented compound Chinese medicine feed additive in sows is beneficial for the improvement of milk quality. [ABSTRACT FROM AUTHOR]