Cows are adapted to degrade structural plant carbohydrates (SC), such as cellulose and hemicelluloses, prevailing in grasses. Yet, the need for energy-dense diets in many intensive dairy production systems has shifted the dairy cattleʼs diet from SC-rich to high levels of starch. Feeding of starch-rich diets increases the risk of ruminal acidosis in cows, and feeding starch in the form of grains intensifies the competition over cereal grains and arable land among different livestock species, as well as between livestock and humans. Besides cellulose and hemicelluloses, grasses are also often rich in water-soluble carbohydrates (WSC), which comprise mono-, di-, oligo-and polysaccharides (fructans). Although the ruminal fermentation profile of monoand disaccharides resembles that of starch, the degradation of oligo-and polysaccharides is slower, and their fermentation elicits a rather protecting effect on ruminal pH. When harvested in an early phase (i.e. ear emergence), grass hay and silages can reach WSC levels up to 150-200 g kg −1 dry matter and energy levels close to starch-rich diets, allowing a significantly reduced inclusion of concentrate supplements. By doing so, this will enhance both rumen health and the sustainability of milk production. However, because the WSC are chemically very heterogeneous, the patterns and extent of their ruminal fermentation are difficult to predict without a clear analytical characterization. This review article aims to summarize both the benefits and potentials, as well as the challenges, with respect to using WSC-rich feedstuffs in the nutrition of dairy cattle and their effects on ruminal fermentation characteristics and milk production.