Background and Objectives: The impact of the duration of symptoms (DOS) on postoperative clinical outcomes of patients with degenerative lumbar spinal diseases is important for determining the optimal timing of surgical intervention; however, the timing remains controversial. This prospective case-control study aimed to investigate the influence of the preoperative DOS on surgical outcomes in minimally invasive surgery-transforaminal lumbar interbody fusion (MIS-TLIF). Materials and Methods: Patients who underwent single-level TLIF for lumbar degenerative diseases between 2017 and 2018 were reviewed. Only patients with full clinical data during the 1-year follow-up period were included. The patients were divided into two groups (DOS < 12 months, group S; DOS ≥ 12 months, group L). The clinical outcomes, including the Oswestry disability index (ODI) and visual analog scale (VAS) for lower back pain, leg pain, and numbness, were investigated preoperatively and at 1, 3, and 6 months, as well as 1 year, after surgery. Furthermore, postoperative patient satisfaction 1 year after surgery was also surveyed. Results: A total of 163 patients were assessed: 60 in group S and 103 in group L. No differences in baseline characteristics and clinical outcomes were found. The ODI and VAS significantly improved from the baseline to each follow-up period (all p < 0.01). Group S had significantly lower ODI scores at 3 months (p = 0.019) and 6 months (p = 0.022). In addition, group S had significantly lower VAS scores for leg pain at 3 months (p = 0.027). In a comparison between both groups, only the patients with cauda equina symptoms showed that ODI and leg pain VAS scores at 3 months after surgery were significantly lower in group S (19.9 ± 9.1 vs. 14.1 ± 12.5; p = 0.037, 7.4 ± 13.9 vs. 14.7 ± 23.1; p = 0.032, respectively). However, the clinical outcomes were not significantly different between both groups 1 year after surgery. Patient satisfaction was also not significantly different between both groups. Conclusions: Patients with a shorter DOS tended to have a significantly slower recovery; however, clinical outcomes 1 year after surgery were good, regardless of the DOS.