There is a balance between DM yield and feed value when choosing types of grasses on a farm depending on the acreages of farmland and types of ruminants to be fed. Therefore, optimisation of the harvest strategy for grass silage is important for profitable dairy farming. Tall fescue has high DM yield and can replace traditional grasses, such as timothy, in Northern Europe in a changing climate as it has been shown to be more drought tolerant. As differences in climate responses previously have been related to differences in cell wall structure between grass species and, consequently, in digestibility, it is highly relevant to compare these species at similar maturity stages and to investigate if a very early harvest date will diminish potential differences between the species. This study evaluated the effects of harvest date and forage species on the concentration of hydroxycinnamic acids in silages and its relationship to feed efficiency of dairy cows. Tall fescue and timothy were harvested at very early date on May 25 or at early date on May 31 in the spring growth cycle. Forty lactating dairy cows were used in a block design. Cows received 1 of 4 treatments: (1) tall fescue harvested at very early date, (2) timothy harvested at very early date, (3) tall fescue harvested at early date, and (4) timothy harvested at early date. Diets were formulated to have the same forage-to-concentrate ratio (49:51 on DM basis). Tall fescue silages showed greater concentrations of DM, ash, and CP than timothy silages. Grasses harvested at early date showed greater concentrations of NDF, ADL, and cell wall than grasses harvested at very early date. Tall fescue silages showed greater concentration of p-coumaric acid and lower in vitro organic matter digestibility (IVOMD) compared to timothy silages. Milk production and composition were not affected by treatments but cows fed tall fescue-based diets showed lower milk protein yield and greater milk urea nitrogen than when timothy-based diets were fed. Furthermore, cows receiving timothy-based diets showed greater feed efficiency compared to cows receiving tall fescue-based diets. Thus, the lower concentration of p-coumaric acid and the higher IVOMD was associated with greater feed efficiency of cows fed timothy-based diets compared to tall fescue-based diets.