Background: Corrective osteotomy around the knee is based on deformity profiles of the femoral and tibial sides. Opening-wedge high tibial osteotomy (OWHTO) can be favored if the outcomes are not different, even if there is a certain degree of abnormal parameters after correction. Purpose/Hypothesis: The purpose of this study was to identify the factors associated with unfavorable radiological outcomes after OWHTO for varus knees. Our hypothesis was that there would be an optimal situation in which double-level osteotomy (DLO) has advantages over isolated OWHTO and an optimal cutoff value of structural parameters for which DLO should be considered in patients with severe varus knees. Study Design: Case-control study; Level of evidence, 3. Methods: The radiological and clinical outcomes of 337 patients who underwent OWHTO were retrospectively evaluated. A subgroup analysis was performed according to the weightbearing line ratio (WBLR) (group 1: <25th percentile; group 2: 25th-75th percentile; and group 3: >75th percentile) and factors associated with unfavorable radiological outcomes. For the assessment of cutoff values of the parameters favoring DLO, unfavorable radiological outcomes were categorized as follows: (1) medial proximal tibial angle (MPTA) >95°, (2) joint-line convergence angle (JLCA) >4° (insufficient medial release), (3) JLCA <0° (medial instability), (4) recurrence of a varus deformity, and (5) lateral hinge fracture. Results: The mean follow-up period was 66.2 ± 19.1 months. A low preoperative WBLR was related to a larger preoperative to postoperative change (Δ) in the WBLR, a larger reduction in coronal translation, a larger ΔMPTA, a wide preoperative lateral joint space, and a narrow preoperative medial joint space ( P < .001, P < .001, P < .001, P = .016, and P = .003, respectively). However, only an MPTA >95° was significantly related to a low WBLR in the subgroup analysis according to unfavorable radiological outcomes ( P = .038). The cutoff value of ΔWBLR causing an MPTA >95° was 46.5%, which showed a good area under the curve of 0.800, with a sensitivity of 74.4% and a specificity of 82.7%. The clinical outcomes significantly improved at the final follow-up compared with those preoperatively, with no significant differences between the WBLR groups. Conclusion: A ΔWBLR ≥46.5% led to an MPTA >95°. However, clinical outcomes were not affected. DLO should be considered if the surgeon desires a postoperative MPTA ≤95°.