Sugarcane varieties differ in their ratooning ability (RA), and it is hypothesized that soil types and harvest seasons impact varieties’ RA. However, the effects of these factors on varieties’ RA remain unclear. This study aimed to assess the RA of different commercial sugarcane varieties (NCo376, N19, N23, N25, and N36), and establish the effects of soils and seasons on ratoon yields of these varieties in Eswatini. Fifteen years data on tons cane per ha per annum (TCHA) and tons sucrose per ha per annum (TSHA) achieved by plant cane and seven ratoon crops were collected from four commercial growers and analysed using linear regression models. The varieties significantly differed in RA. Variety N25, which had the highest plant cane yields (121.3 TCHA and 16.7 TSHA), had the sharpest yield decline over ratoon crops (–2.74 TCHA and −0.33 TSHA), suggesting that this variety is more suitable for short crop cycles. Variety N36 had second highest plant cane yields (111.7 TCHA and 16.4 TSHA) and a lower ratoon yield decline (–1.38 TCHA and −0.16 TSHA) than N25, suggesting that it is suitable for longer ratoon crop cycles. While soil type and harvest season significantly affected the relative yields of varieties, they did not significantly impact their RA, indicating that differences in varieties’ RA were driven by genotype and were relatively stable across environments. This suggests that tests to assess the adaptability of varieties should be conducted in multiple environments, while testing the RA of varieties may be conducted in fewer environments.