The health benefits of fibre consumption are sound, but a more compressive understanding of the individual effects of different fibres is still needed. Arabinoxylan is a complex fibre that provides a wide range of health benefits strongly regulated by its chemical structure. Arabinoxylans can be found in various grains, such as wheat, barley, or corn. This review addresses the influence of the source of origin and extraction process on arabinoxylan structure. The health benefits related to short-chain fatty acid production, microbiota regulation, antioxidant capacity, and blood glucose response control are discussed and correlated to the arabinoxylan’s structure. However, most studies do not investigate the effect of AX as a pure ingredient on food systems, but as fibres containing AXs (such as bran). Therefore, AX’s benefit for human health deserves further investigation. The relationship between arabinoxylan structure and its physicochemical influence on cereal products (pasta, cookies, cakes, bread, and beer) is also discussed. A strong correlation between arabinoxylan’s structural properties (degree of branching, solubility, and molecular mass) and its functionalities in food systems can be observed. There is a need for further studies that address the health implications behind the consumption of arabinoxylan-rich products. Indeed, the food matrix may influence the effects of arabinoxylans in the gastrointestinal tract and determine which specific arabinoxylans can be included in cereal and non-cereal-based food products without being detrimental for product quality.