A triple cropping system, combining spring maize, pearl millet, and twice-cut blast disease resistant Italian ryegrass, was examined for the 2016–2017 and 2017–2018 growing seasons to achieve quality herbage production in Miyazaki, southern Kyushu, Japan. The growth of the three crops reached to harvest, even though typhoon and heavy rainfall occurred. Annual dry matter (DM) yield of the triple crops was 4098 g m−2 and 4349 g m−2 in the first and second cropping seasons, respectively. The observed total digestible nutrients (TDN) were higher in spring maize (up to 68.2% and 76.8%), pearl millet (up to 60.0% and 67.9%), and Italian ryegrass (up to 71.6% and 68.6%), during the first and second season, respectively, leading to an annual TDN yield of 2357 g m−2 and 2938 g m−2. The results suggest that the present established triple cropping system is feasible for obtaining high yields with more digestible nutrients in the forages.