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Biflavonoids and oligomeric flavonoids are the representatives of flavonoids from the diet, which can be classified into several subclasses according to the essential chemical structures. Proanthocyanidin and biflavonoid are two types of representative compounds that are widely distributed in various foods. Although the previous studies have verified that the increase of the polymerization degree of these molecules usually lowered the in vivo bioavailability, the in vivo metabolism of these compounds still remained indeterminate. Some of the most commonly reported in vitro activities of biflavonoids and oligomeric flavonoids were summarized subsequently. And the applications of biflavonoids and oligomeric flavonoids in several processed foods were elucidated because the chemical change during the processing of these compounds can affect the taste and color of the foods. Moreover, the effect on the prevention and relief of some chronic diseases, as well as the uncertain side effects and toxicity of the commercial products being popular on the market, were summarized and analyzed. In addition, the effects of biflavonoids and oligomeric flavonoids on public health, the patents that related to the extract and preparation method, and prospectives and recommendations of their applications were proposed.