The primary aim was to assess survival of the opening wedge high tibial osteotomy (HTO) for medial compartment osteoarthritis. The secondary aim was to identify independent predictors of early (before 12 years) conversion to total knee arthroplasty (TKA). During the 18-year period (1994–2011) 111 opening wedge HTO were performed at the study centre. Mean patient age was 45 years (range 18–68) and the majority were male (84%). Mean follow-up was 12 (range 6–21) years. Failure was defined as conversion to TKA. Kaplan-Meier, Cox regression and receiver operating curve (ROC) analyses were performed. Forty (36%) HTO failed at a mean follow-up of 6.3 (range 1–15) years. The five-year survival rate was 84% (95% confidence interval (CI) 82.6–85.4), 10-year rate 65% (95% CI 63.5–66.5) and 15-year rate 55% (95% CI 53.3–56.7). Cox regression analysis identified older age (p<0.001) and female gender (hazard ratio (HR) 2.37, 95% CI 1.06–5.33, p=0.04) as independent predictors of failure. ROC analysis identified a threshold age of 47 years above which the risk of failure increased significantly (area under curve 0.72, 95% CI 0.62–0.81, p<0.001). Cox regression analysis, adjusting for covariates, identified a significantly greater (HR 2.49, 95% CI 1.26–4.91, p=0.01) risk of failure in patients aged 47 years old or more. The risk of early conversion to TKA after an opening wedge HTO is significantly increased in female patients and those older than 47 years old. These risk factors should be considered pre-operatively and discussed with patients when planning surgical intervention for isolated medial compartment osteoarthritis.