Background: No consensus has been reached regarding the efficacy of indirect decompression through oblique lumbar interbody fusion (OLIF) in severe lumbar spinal stenosis (LSS). This study investigated the impact of preoperative magnetic resonance imaging (MRI)-based grading of central and foraminal stenosis on OLIF outcomes in LSS patients and identified risk factors for postoperative clinical dissatisfaction. Methods: We retrospectively reviewed LSS patients who underwent OLIF with a minimum 1-year follow-up. Clinical scores obtained preoperatively and at 3, 6, 12, and 24 months postoperatively were analyzed using the substantial clinical benefit (SCB) framework. The severity of central and foraminal stenosis in the initial MRI was assessed through qualitative grading systems. Results: Among the 145 patients, with a mean follow-up of 33.7 months, those with severe central stenosis showed a significantly higher proportion of patients achieving SCB in the visual analog scale for leg pain (94.5% versus 83.1%; p = 0.044) at one year postoperatively than those without. However, those with severe foraminal stenosis showed significantly higher Oswestry Disability Index (ODI) scores (p = 0.024), and lower walking ability scores in the Japanese Orthopedic Association Back Pain Evaluation Questionnaire (JOABPEQ) (p = 0.004) at one year postoperatively than those without. The presence of a foraminal osteophyte of the superior articular process (SAP) was a significant risk factor responsible for not achieving SCB in ODI and walking ability in JOABPEQ at one year postoperatively (odds ratio: 0.20 and 0.22, respectively). Conclusions: After OLIF, patients with severe central stenosis showed clinical outcomes comparable to those without. The improvement in ODI and walking ability in JOABPEQ was limited in patients with severe foraminal stenosis. Surgeons should consider direct decompression in cases with the presence of foraminal osteophytes of SAP.