Background: Although opening-wedge high tibial osteotomy (OWHTO) is favored for active patients who expect to return to sports, there is still a lack of robust evidence for factors affecting their recovery. Purpose: To identify (1) risk factors leading to a decreased level of return to preoperative sports after OWHTO and (2) patient characteristics and intraoperative factors influencing patient-reported outcomes after return to sports. Study Design: Case-control study; Level of evidence, 3. Methods: Included were 69 patients who underwent OWHTO and who expected to return to their preoperative level of sports, measured as a Tegner activity level ≥2. All included patients had a minimum of 1 year of follow-up data. Logistic regression analyses were performed to assess the effect of independent variables on the level of return to preoperative sports after surgery; the independent variables were age, sex, body mass index, preoperative Tegner score, preoperative Kellgren-Lawrence grade, preoperative percentage of mechanical axis (%MA), opening gap width, concomitant meniscal treatment, postoperative %MA, postoperative medial proximal tibial angle (MPTA), and postoperative posterior tibial slope. Univariate and multiple regression analyses were performed to assess for influencing factors on postoperative International Knee Documentation Committee (IKDC) subjective scores in patients who were able to return to sports. Results: Of the 69 patients, 51 (73.9%) returned to sports after OWHTO. High preoperative Tegner scores were statistically associated with a decrease in return to sports (odds ratio, 1.494; P = .033). Multiple regression analysis (n = 46 patients) identified that a higher postoperative MPTA was associated with a decreased IKDC subjective score after return to sports ( r = –0.345; P = .019). Conclusion: Higher postoperative MPTA was associated with the worsening of patient-reported outcomes among those patients who did return to their preoperative sports after OWHTO. Also, participation in high-activity sports was confirmed to be a significant risk factor for a decreased rate of return to preoperative sports. These findings can support preoperative planning and intraoperative decision making, particularly for active patients.