Abstract: Let R ∈ Cm×m and S ∈ Cn×n be nontrivial unitary involutions, i.e., RH = R = R−1 = ±Im and SH = S = S−1 = ±In. A ∈ Cm×n is said to be a generalized reflexive (anti-reflexive) matrix if RAS = A (RAS = −A). Let ρ be the set of m × n generalized reflexive (anti-reflexive) matrices. Given X ∈ Cn×p, Z ∈ Cm×p, Y ∈ Cm×q and W ∈ Cn×q, we characterize the matrices A in ρ that minimize AX−Z2+Y HA−WH2, and, given an arbitrary A˜ ∈ Cm×n, we find a unique matrix among the minimizers of AX − Z2 + Y HA − WH2 in ρ that minimizes A − A˜. We also obtain sufficient and necessary conditions for existence of A ∈ ρ such that AX = Z, Y HA = WH, and characterize the set of all such matrices A if the conditions are satisfied. These results are applied to solve a class of left and right inverse eigenproblems for generalized reflexive (anti-reflexive) matrices.