Objective: Limited literature on the effect on clinical and radiological outcomes in cervical endoscopic spine surgery replacing a large percentage of open and microscopic minimally invasive surgery on outcomes in patients for cervical disc herniations and foraminal pathologies. Methods: Retrospective comparative cohort study of two periods of 2015 to 2017 (first generation) is compared to 2018–2020 (second generation) on surgical treatment of degenerative cervical spinal conditions for 132 spinal cases. Basic demographics, preoperative, post-operative 1 week, 3 months and final follow-up of patients’ clinical outcomes in terms of Visual Analog Scale Pain Score, Neck Disability Index, Japanese Orthopaedic Association Score and MacNab’s Criteria were evaluated. Results: In the first generation, 50 cases of cervical disc herniation and foraminal stenosis with 70% open anterior cervical discectomy fusion or disc replacement 30% of the cases underwent posterior cervical endoscopic procedures with complication rate of 2%. In the second generation, 82 cases of cervical disc herniation and foraminal stenosis with 7% open anterior cervical discectomy fusion or disc replacement 93% of the cases underwent posterior cervical endoscopic procedures with complication rate of 6%. Compared to preoperative score, motor, JOA, VAS and NDI scores all statistically significant improved within the individual cohort. Compared to the first generation, the second generation has statistically significant improved VAS of 0.326+/−0.146 at 3 months and 0.648+/−0.163 at final follow-up and statistically significant improved NDI of 2.81+/−1.15 at final follow-up, p < 0.05. Conclusions: Generation change of increasing percentage of endoscopic surgeries and expansion of endoscopic spinal indications over open surgeries in degenerative spinal conditions and disc herniations are possible as a surgeon gets more experience with endoscopic spine surgery producing good clinical outcomes.