We aimed to evaluate the timing, operative details, and outcomes of total knee arthroplasty (TKA) in patients with prior ligamentous knee surgery (LKS). All consecutive patients undergoing TKA with prior LKS at a single institution were identified from a large prospectively collected database. Patients were matched on a 2:1 basis according to age, sex, and body mass index to a group of patients without previous LKS undergoing primary TKA. A total of 39 patients with prior LKS and a mean age of 55.6 years (range: 42.8–76.4) were identified and matched with 78 patients without LKS with a mean age of 57.6 years (range: 44.0–79.4) undergoing primary TKA (p = 0.24). Significantly more posterior stabilized implants were used in patients with LKS compared with control patients (29 [74.3%] vs. 27 [34.6%], p < 0.001). In the LKS group, 15 patients (38.4%) required hardware removal. Postoperative complications and rate of further surgery were greater in the LCS group, but the difference was not significant (10.6 vs. 6.4%, p = 0.25). Mean difference in pre- to postoperative knee flexion and clinical outcome scores (12-item Short Form Survey, International Knee Documentation Committee, and Oxford Knee Score) were similar between the two groups, with no cases of loosening or osteolysis. TKA with prior LKS often warranted hardware removal and generally more constrained implants. Those patients with prior LKS undergoing subsequent TKA have higher complication rates and an increased rate of subsequent surgery related to post-TKA stiffness.