Social functioning and personal satisfaction about quality of life are issues in the spotlight in most fields of otolaryngology. However, in ear surgery, few studies performed standardised measurements through interviews and validated questionnaires. We enrolled 81 patients undergoing tympanomastoidectomy from January 2011 to December 2014, at the “A. Gemelli” Hospital of the Catholic University, Rome. 50 patients (61.7%) underwent non-obliterative Canal Wall Down (CWD) mastoidectomy, whereas 31 patients (38.3%) underwent Canal Wall Up (CWU) mastoidectomy. We administered the Chronic Ear Survey (CES) 3 and 12-months post-operatively and the Chronic Otitis Media Outcome Test-15 (COMOT-15) 12 months post-operatively. Results were compared to hearing threshold, sex and age. In the CWD Group, significant improvements were observed in all CES subscale scores and total scores over time (p < 0.001) whereas in the CWU Group we found a partial improvement. Inter-group comparison showed no significant differences in administration of CES in CWD vs CWU (p > 0.05 for all subsections and overall scores). A significant difference was found only in the COMOT-15 “Hearing Function” subsection, in favour of CWU over CWD (61 vs 39 respectively; p < 0.05). A significant association was found between PTA and COMOT-15 “Hearing Function” subsection scores. According to our results, a significant difference in the post-operative QoL between CWD and CWU should not be taken for granted.