In this paper, we address the stability of an elastic thin annular plate stretched by two point loads that are located on the outer boundary. A roller support is considered on the outer boundary while the inner edge of the plate is free. Muskhelishvili’s theory of complex potentials has been applied to obtain a solution of the plane problem in the form of a power series. The buckling problem has been solved using the Rayleigh–Ritz method, based on the energy criterion. The critical Euler force and the respective buckling mode have been computed. Dependence between the critical force and the relative orifice size has been illustrated. Analysis of the results has shown that a symmetric buckling mode takes place for a sufficiently large hole, with the greatest deflection observed around the hole along the force line. However, an antisymmetric buckling mode occurs for relatively small holes, with the greatest deflection being along a line that is orthogonal to the force line.