The object of this study is to evaluate the long-term outcome of hind limb weight-bearing function and progression of stifle osteoarthritis (OA) after tibial plateau leveling osteotomy (TPLO). Groups were classified by the degree of cranial cruciate ligament (CrCL) damage and presence or absence of medial meniscus damage as macroscopically evaluated during surgery. Weight-bearing function was assessed via the peak vertical force (PVF), and OA progression was assessed via the radiographic OA score (OAS) preoperatively and 1, 3, 6, 12, 18, 24, and 36 months postoperatively. In all stifles, PVF was significantly higher within 6 months postoperatively than preoperatively, and this high ratio was maintained for 36 months. The OAS was significantly higher 24 months postoperatively than preoperatively in stifles with a partial CrCL tear, and significantly increased at each timepoint after 3 months postoperatively in stifles with complete CrCL rupture. The OAS remained consistently lower in stifles with a partial CrCL tear and no treatment of the medial meniscus than in stifles with complete rupture. Thus, after TPLO, the weight-bearing function improved in the early postoperative period and was maintained for as long as 36 months. Although OA progressed over time after TPLO, the progression was more gradual in stifles with partial tears than in those with complete rupture. Canine patients would benefit from earlier surgical intervention through development of technology that enables early detection of ligament degeneration.