Oral diseases, including dental caries, periodontal disease, and tooth loss, affect the majority of the population and can affect a person’s overall health. Raisins contain polyphenols, flavonoids, and high levels of iron that may benefit human health. However, their oral health benefits are less well understood. We hypothesized that raisins contain antimicrobial phytochemicals capable of suppressing oral pathogens associated with caries or periodontal diseases and thus benefit oral health. Through antimicrobial assay-guided fractionation and purification, compounds identified with growth inhibition against oral pathogens were oleanolic acid, oleanolic aldehyde, linoleic acid, linolenic acid, betulin, betulinic acid, 5-(hydroxymethyl)-2-furfural, rutin, beta-sitosterol, and beta-sitosterol glucoside. Oleanolic acid suppressed in vitro adherence of cariogenic Streptococcus mutans biofilm. When the effect of raisins and raisin-containing bran cereal on in vivo plaque acidogenicity was examined in 7- to 11-y-old children, it was found that raisins did not reduce the plaque pH decline below pH 6 over the 30-min test period. Compared with commercial bran flakes or raisin bran cereal, a lower plaque pH drop was noted in children who consumed a raisin and bran flake mixture when no sugar was added (P < 0.05). Grape seed extract, high in proanthocyanidins, positively affected the in vitro demineralization and/or remineralization processes of artificial root caries lesions, suggesting its potential as a promising natural agent for noninvasive root caries therapy. Raisins represent a healthy alternative to the commonly consumed sugary snack foods.