OBJECTIVE Few reports discuss the characteristics of repeated recidivism of cholesteatoma. We describe the clinical characteristics of patients with cholesteatoma who experienced at least two recidivism episodes after initial surgery for cholesteatoma requiring canal wall reconstruction. METHODS We reviewed the medical records of 11 patients who underwent surgery for cholesteatoma with canal wall reconstruction at our department between April 2008 and March 2018 and subsequently experienced two relapses that necessitated revision surgery involving tympanomastoidectomy with canal reconstruction. Patient age at the time of the first surgery ranged from 6 to 56 (mean, 25.7) years. Seven (63.6%) of the 11 patients were male. These 11 patients were classified according to the type of recidivism, and their characteristics (pathology, operation date, operation method, pattern of relapse, and position of recurrence) were investigated. RESULTS Four cases involved secondary residual cholesteatoma, with the mean interval between the first revision surgery and the second revision surgery being 23.8 (range, 11-39) months. Secondary residual sites included the anterior tympanic cavity, tympanic sinus, and anterior end of the reconstructed cartilage of the canal wall. The other seven cases involved secondary recurrence, with the mean interval between the first and the second revision surgery being 26.1 (range, 12-57) months. The sites of recurrence were at the edges of the reconstructed cartilage. One notable case involved the cartilage junction, leading us to hypothesize that retraction of the temporal muscle flap and the patulous Eustachian tube was the underlying cause. CONCLUSIONS For residual cholesteatoma, strict measures are necessary to maintain the operation under clear view, and more careful follow-up is necessary in patients who have had previous surgery at another hospital. For recurrent cholesteatoma, it was recognized that Eustachian tube function must be ascertained in advance, and careful observation of the reconstructed cartilage edge is necessary.