OBJECTIVE:: To review a single surgeonʼs experience with T-tube placement through cartilage tympanoplasty versus native tympanic membrane for long-term ventilation of the chronic ear and residual perforation rates following tube removal. STUDY DESIGN:: Retrospective chart review. SETTING:: Two tertiary referral centers. PATIENTS:: One hundred sixteen patients (4–71 yr of age) who underwent either total island cartilage tympanoplasty or posterior palisade cartilage tympanoplasty with T-tube placement primarily or secondarily from 1998 to 2016. MAIN OUTCOME MEASURES:: Long-term outcome of each T-tube was recorded with respect to retention and patency, and tympanic membrane status following either tube removal or extrusion. Audiometric data, age, sex, diagnosis, and procedure(s) performed were considered. RESULTS:: There were 116 patients (122 total ears and 139 total T-tubes) included: 57 ears underwent total island cartilage tympanoplasty with tube placed through cartilage and 65 ears underwent posterior island graft with tube placed through native tympanic membrane. Sixty-eight T-tubes were placed in the total island cartilage group with three (4.4%) residual perforations following removal. Seventy-one T-tubes were placed in the posterior palisade graft group with six residual perforations (8.5%) following removal or extrusion. The mean retention rate for the T-tubes was 3.93 years for the total island tympanoplasty group and 3.58 years for the posterior palisade tympanoplasty group. The mean follow-up for total island tympanoplasty and posterior palisade tympanoplasty was 5.36 and 5.66 years, respectively. CONCLUSION:: Our data suggest that T-tube placement through cartilage tympanoplasty is worthwhile providing long-term ventilation to the middle ear and portends no higher risk for residual perforation than T-tube placement through native tympanic membrane.