Proximal row carpectomy (PRC) and four-corner arthrodesis (FCA) are common surgical procedures used to treat degenerative wrist conditions; however, complications and failures can occur. This study aimed to investigate and compare the long-term rate of secondary surgeries including conversion to total wrist arthrodesis in patients who underwent PRC or FCA. A retrospective chart review of all patients who underwent PRC or FCA in the past 20 years at a tertiary referral institution and associated Veterans Affairs (VA) hospital was performed. Patient demographics, comorbidities, surgical indications, and associated complications were tabulated. Patients were contacted via phone to obtain additional follow-up information regarding any additional surgeries, 10-point visual analog scale (VAS) for pain, quick Disabilities of the Arm, Shoulder, and Hand (quickDASH) scores, hand dominance, and occupational data. A total of 123 wrists made up the final dataset. Sixty-two wrists treated with PRC and 61 wrists treated with FCA were reviewed at a mean follow-up of 8.2 years. We did not find a significant difference in the rate of conversion to total wrist arthrodesis between the PRC (14.5%) and FCA (19.5%, = 0.51) cohorts. Secondary operations were significantly greater in the FCA group (34.4%) compared with the PRC group (16.1%, = 0.02). Females were 2.6 times more likely than males to undergo secondary operations when controlling for surgical procedure and smoking status ( = 0.04). We did not detect a significant difference in VAS pain or in quickDASH scores between the two groups ( = 0.35, 0.48, respectively). PRC and FCA have comparable patient reported outcomes and wrist arthrodesis conversion rates at a mean follow-up of 8.2 years. In contrast, the FCA patient group had a significantly higher rate of secondary operations, including those for nonunion, symptomatic hardware, and other implant-related issues, when combined with wrist arthrodesis conversion. Level IV, therapeutic study.