Chopart amputations were first performed for treatment of a non-salvageable distal foot but became unfavorable because of the development of equinovarus contractures and ulcerations. The majority of below-knee amputations today occur in ambulatory patients with diabetes in which a Chopart amputation may be a viable option; however, the durability of the residual limb is questionable. The authors undertook a systematic review of electronic databases and other relevant sources to identify material relating to the factors associated with a successful Chopart amputation in ambulatory patients with diabetes. Studies were eligible for inclusion only if they consecutively enrolled ambulatory patients with diabetes who underwent a Chopart amputation, regardless of etiology, with or without any tendinous or osseous balancing performed and had a mean follow-up of ≥12 months duration. Four studies involving 74 patients/feet were identified that met the inclusion criteria with a weighted mean follow-up of 21.1 months. The efficacy of tendinous and/or osseous balancing could not be assessed because of the lack of comparable techniques. However, review of the included studies supports that a residual functional limb can be maintained for ≥12 months with the use of a properly fitting high-profile prosthetic device for lifelong ambulation.