Background: Large defects of the middle cheek may prove difficult to repair. Too wide for primary closure, such defects pose challenging reconstructive options because there are no cosmetic unit boundaries in which to camouflage incision lines without resorting to widely undermined flaps. Objective: This article summarizes our experience with the Z-plasty and double Z-plasty transposition flaps for reconstruction of the cheek. Methods: The Z-plasty transposition flap was used immediately after Mohs micrographic surgery to repair 14 defects of the middle cheek caused by basal cell carcinoma (n = 12) or squamous cell carcinoma (n = 2). In all cases, primary closure of the defect would have resulted in excessively long scars, scars oriented perpendicular to relaxed skin tension lines, and/or free-margin distortion. In 4 of these cases, a double Z-plasty was used. Results: The cosmetic and functional outcomes were judged from good to excellent by patient and surgeon. No cases of infection occurred. In one patient, minor superficial tip necrosis healed without incident. A “spit” subcutaneous suture at one flap tip of another patient left a small nodular scar, which was primarily excised and healed well. Conclusions: The Z-plasty and double Z-plasty transposition flaps offer excellent primary reconstructive modalities for the repair of geographically isolated defects of the cheek that are large or misoriented for primary side-to-side closure. The theoretical and practical geometric characteristics of the Z-plasty transposition require preparation and practice to achieve consistently satisfying results. (J Am Acad Dermatol 2002;46:738-42.)