Grasslands are important for sustainable milk and meat production as well as for providing other ecosystem services. One of the most productive components of short-term grasslands is Italian ryegrass (Lolium multiflorum subsp. italicum Lam.), offering high yield, excellent feed value, and high palatability to animals but low tolerance to abiotic stress. Global climate warming opens new opportunities and could be beneficial in increasing the potential of biomass production. In this study, we aimed to assess an Italian ryegrass cultivar of Lithuanian origin, ‘Ugnė’, for productivity and yield stability, with special emphasis on their relationship with climatic factors over a period of 14 years. The average winter temperatures and total spring precipitation explained 51% of the first-cut dry matter yield (DMY) variance. Second- and third-cut DMYs were associated with average temperature only. Italian ryegrass cv. ‘Ugnė’ demonstrated the potential to produce high dry matter yields after warm winters and withstand summer drought spells under Lithuanian conditions. However, mid-to-late-summer heat waves might reduce productivity and should be taken into consideration when breeding new Italian ryegrass cultivars.