Introduction Tandem spinal stenosis (TSS) refers to the narrowing of the spinal canal at two distinct anatomic areas. Symptoms can present due to either cervical myelopathy or lumbar stenosis. Consequently, determining the symptomatic anatomical levels requiring surgery can pose a challenge. We sought to identify the surgical approach associated with better patient-reported outcomes. Materials and Methods The Information Management System was queried using the International Classification of Diseases Ninth and Tenth Edition codes to identify patients who underwent simultaneous or staged decompression surgery for TSS between 2011 and 2020. Patient records were reviewed to collect data on age, sex, comorbidities, surgical approach, modified Japanese Orthopedic Association (mJOA) score, and complications. The mJOA is a validated composite assessment used to quantify postoperative neurological status. Multivariable regression models were utilized to identify factors associated with better postoperative neurological recovery. Results Among 42 patients included in the analytical cohort, 33 (78.6%) underwent simultaneous cervical and lumbar decompression, while 9 (21.4%) underwent staged decompression (cervical followed by lumbar). The patient's age, sex, comorbid conditions, and American Society of Anesthesiologists level were similar between the two groups. Furthermore, simultaneous decompression was associated with higher blood loss (676.97 vs. 584.44 mL) and an increased need for transfusion (259.09 vs. 111.11 mL) compared with staged decompression. Moreover, patients who underwent simultaneous decompression experienced a higher number of postoperative complications (10 vs. 1; p = 0.024). Notably, postoperative mJOA scores improved in both groups; however, the improvement was more pronounced in the staged group (mJOA score: 15.16% [ ± 2.18] vs. 16.56% [ ± 1.59]). On follow-up visits, patients who underwent staged decompression showed better recovery rates (mJOA score: 78.20% [ ± 24.45] vs. 59.75% [ ± 25.05]). Conclusion The patient's clinical history and examination findings should be the main determinants of surgical decision-making. Our study showed a slightly higher postoperative mJOA score and a recovery rate with fewer complications in staged decompression of TSS.