Osteotomy cuts are typically made using a saw, and the meeting point acts as a focus for the concentration of stress and failure. We have studied the impact of different designs of osteotomy cut. Cadaver sheep tibias were scanned by computed tomography (CT) and transformed into a computer-aided design (CAD) model. A standard marginal resection defect was created and then modified, and a finite element analysis made. The relative stress concentrations at the intersection of osteotomy cuts were recorded using principal stresses S1, S3, and von Mises stress, von Mises under both 4-point bending and torsion testing. The osteotomy designs studied were: right-angled and bevelled osteotomy end cuts, overcutting, and a stop drill hole. Peak stress values for 4-point bending and torsion were 24–30% greater at the right-angled osteotomy than the bevelled end cut. Overcutting dramatically increased peak stress values caused by bending and torsion by 48% and 71%, respectively. Substantially lower concentrations of stress were noted with a stop hole using both a 90° (bending 38% and torsion 56%), and a tangential (bending 58% and torsion 60%) cut. A bevelled osteotomy has substantially lower concentrations of stress than a right-angled osteotomy. It is important to avoid creating an overcut as this causes an appreciable increase in the concentration of stress, while a stop drill hole substantially reduces the stress. The creation of a stop hole and the use of judicious bevelling techniques are modifications in the design of an osteotomy that are readily applicable to surgical practice.