Background: As the number of surgical options in glaucoma treatment is continuously rising, evidence regarding distinctive features of these surgeries is becoming more and more important for clinicians to choose the right surgical treatment for each individual patient. Methods: For this retrospective data analysis, we included glaucoma patients treated with either continuous wave (CW-TSCPC) or micropulse transscleral cyclophotocoagulation (MP-TSCPC) in an inpatient setting. Pain intensity was assessed using a numeric rating scale (NRS) ranging from 0 (no pain) to 10 (worst imaginable pain) during hospitalization. CW-TSCPC was performed using OcuLight® Six (IRIDEX Corporation, Mountain View, CA, USA) and MP-TSCPC was performed using the IRIDEX® Cyclo-G6 System (IRIDEX Corporation, Mountain View, CA, USA). Results: A total of 243 consecutive cases of TSCPC were included. Of these, 144 (59.26%) were treated with CW-TSCPC and 99 (40.74%) with MP-TSCPC. Using the univariable model, the risk for postoperative pain was observed to be lower in MP-TSCPC compared with CW-TSCPC (unadjusted: OR 0.46, 95% CI 0.24–0.84, p = 0.017), but this did not hold using the multivariable model (adjusted: OR 0.52, 95% CI 0.27–1.02, p = 0.056). Simultaneously conducted anterior retinal cryotherapy was associated with a higher risk for postoperative pain (OR 4.41, 95% CI 2.01–9.69, p < 0.001). Conclusions: We found that the occurrence of postoperative pain was not different in CW-TSCPC compared with MP-TSCPC in a multivariable model. In cases of simultaneous anterior retinal cryotherapy, the risk for postoperative pain was significantly higher.