The analysis of the stress distribution around a defect near the contact area and the effect of the defect on the contact pressure distribution is one of the most important problems in tribology. In this work, for a contact problem of an elastic half-plane containing a circular hole, the hoop stress around the hole is calculated using the singular integral equations method. For the contact pressure distribution, two models are considered. One is the Hertzian contact pressure distribution, and in the other, the effect of the circular hole on the contact pressure distribution is taken into consideration. In these analyses, the circular hole is replaced with a continuous array of edge dislocations and the traction-free condition on the surface of the circular hole is reduced into a set of singular integral equations in which the dislocation density functions are unknown. In solving the singular integral equations numerically, the Hilbert inversion formula is utilized. From the results of the numerical calculations, it has been clarified that the hoop stress around the hole becomes tensile at some parts, and that in some cases, the contact pressure deviates from the Hertzian one due to the existence of the circular hole.