To identify rice (Oryza sativa L.) cultivars suitable for Italian ryegrass (Lolium multiflorum Lam.)-rice double cropping systems, we investigated the yield and grain quality of four different midseason maturing rice cultivars ('Daebo', 'Haepum', 'Haiami', and 'Samdeog') and four midseason-to-late maturing rice cultivars ('Hyunpoom', 'Saeilmi', 'Saenuri', and 'Samkwang') in single rice cropping and Italian ryegrass-rice double cropping systems in paddy fields of Miryang, South Korea. We found that organic matter and available P2O5 content slightly decreased, whereas Na content increased, in the soil where Italian ryegrass was cultivated during winter compared to that in the soil that remained fallow during winter. The pH, electrical conductivity, organic matter, and contents of K+, Ca2+, Mg2+, and Na+ decreased, whereas the available P2O5 content slightly increased, in the soil where rice was harvested in both single and double cropping systems. However, compared to the optimum soil conditions for rice cultivation, available P2O5 and K+ content were high and Mg2+ content was low in both single and double cropping systems. At the heading stage, the culm length and leaf color slightly increased in most of the rice cultivars, whereas the panicle length and number slightly decreased, in the double cropped system. After harvesting, spikelet number and milled rice yield did not show a significant difference between single and double cropping systems. However, the ripened grain rate and weight per thousand grains increased slightly in the 'Saeilmi' and 'Samkwang' cultivars but remained either stable or slightly low in other cultivars in the double cropping system. The milled rice yield was high (> 500 kg/10a) in 'Daebo' and 'Haepum' among midseason maturing rice cultivars, and in 'Saeilmi' and 'Saenuri' among midseason-to-late maturing rice cultivars, in both single and double cropping systems. The head rice rate was high in midseason maturing rice cultivars in the double cropping systems, reaching > 70% in 'Haepum' and 'Haiami' cultivars, whereas it decreased in most midseason-to-late maturing rice cultivars (excluding 'Samkwang' cultivar), in double cropping systems. Particularly, it exceeded > 70% in the 'Saenuri' cultivar in both single and double cropping systems. The protein content in milled rice increased, whereas the amylose content either remained stable or slightly increased, in double cropping systems. The Toyo taste value decreased in all midseason-to-late maturing rice cultivars and slightly increased in the 'Daebo' and 'Haiami' cultivars among midseason maturing rice cultivars in double cropping systems. However, Toyo taste values in the 'Haepum', 'Haiami', and 'Saenuri' cultivars exceeding > 80% in both single and double cropping systems. Therefore, we recommend 'Haepum', 'Haiami', and 'Saenuri' cultivars as candidates for Italian ryegrass-rice double cropping systems due to high yield, head rice rate, and Toyo taste value.