The Boussinesq problem, namely the indentation of a flat-ended cylindrical punch into a viscoelastic half-space is studied. We assume a linear viscoelastic model wherein the linearized strain is expressed as a function of the stress. However, this expression is not invertible, which makes the problem very interesting. Based on the Papkovich–Neuber representation in potential theory and using the Fourier–Bessel transform for axisymmetric bodies, an analytical solution of the resulting time-dependent integral equation is constructed. Consequently, distribution of the displacement and the stress fields in the half space with respect to time is obtained in the closed form.