This paper describes experimental results on the way immiscible drops of a Newtonian fluid can deform and breakup when subject to oscillatory shear deformation. The paper also reports a matching three-dimensional numerical simulation of corresponding events. Using an optical shearing apparatus and a modified rheometer, experimental observations on the deformation of drops with a viscosity ratio of unity were carried out for a range of strain amplitudes and frequencies. For moderate strain deformations, it was discovered experimentally that the drop deformation oscillates between a maximum and a nonzero minimum deformation parameter and that the numerical simulation was able to capture both this and start up effects. For large strain deformations it was experimentally observed that breakup occurred only by one mechanism; namely, end pinching, and this was successfully matched by the numerical simulation. The results for oscillatory deformation and breakup are compared with those obtained in steady shear.