Introduction Deep infiltrating endometriosis (DIE) affects between 3.8% and 37% of all endometriosis patients, mostly affecting rectovaginal septum or retrocervical space and characterized by the severe endometriosis-related complaints. Nowadays, generally managed with surgery. However, this is associated with a risk of postoperative complications. To better evaluate intra- and postoperative complications and outcomes for rectovaginal (RVE) and retrocervical endometriosis (RCE), the preoperative management should be accurately described and compared. Methodology This is a cohort retrospective study performed at the Endometriosis Centre of Charite-University Clinic, Berlin. 34 patients were investigated in their reproductive age,n = 19 with RVE andn = 15 RCE, operated between 2011 and 2015. The surgical approach was divergent in both groups. Single laparoscopy was performed in RCE patients (RCEP) and vaginal assisted laparoscopy in RVE patients (RVEP). Long-term postoperative outcome included complications, fertility rate and recurrence rate. Results The median follow-up time was three years (y). Symptom-free status was revealed inn = 12 RVEP andn = 9 RCEP. Postoperatively, endometriosis-related complaints were presented inn = 7 RVEP andn = 6 RCEP, but with significant pain relief. From n = 8 RVE patients seeking fertility, pregnancy occurred in n = 7 and from n = 9 RCEP pregnancy appeared inn = 5 patients in the meantime of 6 months. Postoperative complications were reported inn = 1 RVEP with early postoperative bleeding, after ureter leakage andn = 1 RCEP with postoperative anastomotic insufficiency. The postoperative recurrence rate was equivalent to zero. Conclusion The appropriate surgical approach for each group, preserving anatomy and functionality of the organs, seems to be very essential and efficient.