This study investigated cow longevity, culling reasons, and risk factors influencing culling in South African Holstein and Jersey dairy herds. Lactation records of 1,150,625 Jersey and 1,534,875 Holstein cows from 1864 herds, recorded through the National Milk Recording Scheme during the period 2000 to 2019, were analyzed. Longevity was calculated as length of productive life and number of completed lactations. Logistic binary regression was conducted to estimate the odds ratios (OR) for culling among different calving seasons, parities, and herd sizes. Holstein cows had mean productive life of 739.33 ± 434.31 days and 2.37 ± 1.08 lactations, while Jersey cows averaged 696.81 ± 415.44 days productive life and 2.47 ± 1.13 lactations. Leading reasons for culling were infertility (37.94 ± 0.48% Holstein; 30.46 ± 0.63% Jersey), mastitis (18.15 ± 0.38% Holstein and 18.16 ± 0.53% Jersey), and low milk yield (11.76 ± 0.32% Holstein and 19.76 ± 0.55% Jersey). Summer calving, third parity, and small herd size had the highest odds of culling. These findings suggest that herd management practices and selection objectives in South Africa should place high emphasis on cow fertility and udder health. Furthermore, cows calving in summer and those in third parity or small herds require particular attention to minimize culling. Such measures may help to reduce involuntary culling rates and thus increase herd profitability as well as dairy industry sustainability.