We calculate the Casimir interaction energy in d = 2 spatial dimensions between two (zero-width) mirrors, one flat, and the other slightly curved, upon which imperfect conductor boundary conditions are imposed for an Electromagnetic (EM) field. Our main result is a second-order Derivative Expansion (DE) approximation for the Casimir energy, which is studied in different interesting limits. In particular, we focus on the emergence of a non-analyticity beyond the leading-order term in the DE, when approaching the limit of perfectly-conducting mirrors. We also show that the system considered is equivalent to a dual one, consisting of a massless real scalar field satisfying imperfect Neumann conditions (on the very same boundaries). Therefore, the results obtained for the EM field hold also true for the scalar field model.