We calculate corrections to the fermion propagator and to the Green's functions of all fermion bilinear operators of the form $\bar\Psi \Gamma \Psi$, to one-loop in perturbation theory. We employ the Wilson/clover action for fermions and a family of Symanzik improved actions for gluons. The novel aspect of our calculations is that they are carried out to second order in the lattice spacing, $O(a^2)$. Consequently, they have addressed a number of new issues, most notably the appearance of loop integrands with strong IR divergences (convergent only beyond 6 dimensions). Such integrands are not present in $O(a^1)$ improvement calculations; there, IR divergent terms are seen to have the same structure as in the $O(a^0)$ case, by virtue of parity under integration, and they can thus be handled by well-known techniques. We explain how to correctly extract the full $O(a^2)$ dependence; in fact, our method is generalizable to any order in $a$. The $O(a^2)$ corrections to the quark propagator and Green's functions computed in this paper are useful to improve the nonperturbative RI-MOM determination of renormalization constants for quark bilinear operators. Our results depend on a large number of parameters: coupling constant, number of colors, lattice spacing, external momentum, clover parameter, Symanzik coefficients, gauge parameter. To make these results most easily accessible to the reader, we have included them in the distribution package of this paper, as an ASCII file named: Oa2results.m ; the file is best perused as Mathematica input.