Background: Tympanic membrane retraction pockets (RPs) are localized invaginations resulting from chronic Eustachian tube dysfunction and progressive loss of tympanic membrane elasticity. Without timely management, they may progress to ossicular chain erosion, conductive hearing loss, or secondary cholesteatoma. Methods: We conducted a retrospective descriptive study of 74 patients with non-cholesteatomatous tympanic membrane RPs managed surgically at the Department of Otorhinolaryngology and Head and Neck Surgery, 20 August 1953 Hospital, Ibn Rochd University Hospital, Casablanca, Morocco. Cases with cholesteatoma, incomplete records, or follow-up < 12 months were excluded. Primary outcomes were anatomical success (tympanic membrane closure) and postoperative air–bone gap (ABG) at 12 months. Results: The mean age was 35 years, with a female predominance (65%). The leading symptoms were hearing loss (82.4%) and otorrhea (89.2%). RPs were most commonly located at the attic (39.2%) and in the posterior quadrants (31.1%). Conductive hearing loss was present in 59.5% of patients and mixed hearing loss in 32.4%. Ossicular chain disruption was identified intraoperatively in 55.4% of cases, predominantly involving the incus. Anatomical success was achieved in 93.2% of patients. The mean ABG in improved from 25.6 dB preoperatively to 17.3 dB postoperatively (mean gain: 8.3 dB). Secondary cholesteatoma occurred in 1.4% of cases. Conclusion: Non-cholesteatomatous RPs are progressive lesions with a significant risk of ossicular damage and secondary cholesteatoma. Cartilage tympanoplasty achieved anatomical success in 93.2% of cases. However, functional recovery remained modest overall, given the high rate of ossicular chain disruption observed intraoperatively, underscoring the importance of early surgical intervention before irreversible ossicular damage occurs.