Background: Joint replacement surgeries have been known to be some of the most painful surgical procedures. Therefore, the options for postoperative pain management are of great importance for patients undergoing total knee arthroplasty (TKA). Despite successful surgery, up to 30% of the patients are not satisfied after the operation. The aim of this study is to assess pain development within the first 4 weeks after TKA in order to gain a better understanding and detect possible influencing factors. Methods: A total of 103 patients were included in this prospective cohort study. Postoperative pain was indicated using a numeric rating scale (NRS). Furthermore, demographic data and perioperative parameters were correlated with the reported postoperative pain. Results: The evaluation of postoperative pain scores showed a constant decrease in the first postoperative week (mean NRS score of 5.8 on day 1 to a mean NRS score of 4.6 on day 8). On day 9, the pain increased again. Thereafter, a continuous decrease in pain intensity from day 10 on was noted (continuous to a mean NRS score of 3.0 on day 29). A significant association was found between postoperative pain intensity and gender, body mass index (BMI), and preoperative leg axis. Conclusions: The increasing pain score after the first postoperative week is most likely due to more intensive mobilization and physiotherapy in the rehabilitation department. Patients that were female, had a low BMI, and a preoperative valgus leg axis showed a significantly higher postoperative pain scores. Pain management should consider these results in the future to improve patient satisfaction in the postoperative course after TKA.