This experiment was carried out to investigate the effect of harvesting time of Italian ryegrass (Lolium multiflorum Lam; IRG) in spring on dry matter (DM) yield. IRG cultivars ‘Kowinearly’ and ‘Greenfarm’ were seeded at 50 kg/ha and grown on rice paddy fields. There was no difference in growth characteristics between both varieties before winter. However, cold tolerance of Kowinearly was higher than that of Greenfarm, as demonstrated by post-wintering growth characteristics. The heading date of both varieties was affected by the spring weather. The IRG was harvested three times at 5-day intervals beginning from 9 May. The DM yield of Greenfarm was 6,306; 7,335; and 8,109 kg/ha, and that of Kowinearly was 7,498; 9,196; and 10,449 kg/ha at the three consecutive harvests. The delay of the harvesting time for 5 and 10 days increased the DM yield of Greenfarm by 16% and 29% and that of Kowinearly by 23% and 39%, respectively, compared to the yield at first harvest (p < 0.05). Therefore, IRG harvest later than early to mid-May is expected to increase productivity. The feed values of Greenfarm were: 12.2% of crude protein (CP), 34.5% of acid detergent fiber (ADF), 57.7% of neutral detergent fiber (NDF), 61.6% of total digestible nutrients (TDN), and 72.3% of in vitro DM digestibility (IVDMD). For Kowinearly, these values were 16.4% of CP, 30.4% of ADF, 52.7% of NDF, 64.9% of TDN and 79.0% of IVDMD.