Background: Postoperative pain is an unpleasant experience for the patient and impairs postoperative functional outcomes. The current literature on the influence of preoperative predictors on postoperative pain outcomes remains limited. This study aimed to identify sociodemographic, clinical, psychological, and temperamental predictors of postoperative pain in patients undergoing surgery for degenerative disc disease (DDD). Methods: Eighty-one adults with DDD, qualified for neurosurgical intervention, were enrolled. All patients underwent neurological and psychiatric evaluations, as well as preoperative pain assessments using the Visual Analogue Scale (VAS) and the West Haven-Yale Multidimensional Pain Inventory (WHYMPI). Psychological assessments included the Perceived Stress Scale, Hospital Anxiety and Depression Scale, Somatic Symptom Scale, temperament, and personality inventories (e.g., FCB-TI, NEO-FFI), and cognitive tests (Trail Making Test, Digit Span Test). Postoperative pain was re-evaluated with the VAS 12 weeks after surgery. Data were analyzed using univariate and multivariate statistical methods. Results: Univariate analyses revealed significant differences between the defined groups regarding lack of improvement of pain 12 weeks after surgery compared to preoperative VAS, systolic blood pressure, and four scales from the WHYMPI. However, stepwise logistic regression identified only preoperative VAS score as an independent predictor of postoperative pain improvement. Receiver Operating Characteristic analysis and Youden’s index indicated a preoperative VAS cut-off score of 6 as the most predictive. Conclusions: A VAS score of 6 or more before surgery independently predicts the absence of chronic pain 12 weeks postoperatively for patients without neurological deficits. Moreover, given the complexity of this topic, further prospective, randomized controlled research is essential.