The proposed optimal algorithm for the digitizing of analog filters is based on two existing filter design methods: the extended window design (EWD) and the matched–pole (MP) frequency sampling design. The latter is closely related to the filter design with iterative weighted least squares (WLS). The optimization is performed with an original MP design that yields an equiripple digitizing error. Then, a drastic reduction of the digitizing error is achieved through the introduction of a fractional time shift that minimizes the magnitude of the equiripple error within a given frequency interval. The optimal parameters thus obtained can be used to generate the EWD equations, together with a variable fractional delay output, as described in an earlier paper. Finally, in contrast to the WLS procedure, which relies on a “good guess” of the weighting function, the MP optimization is straightforward.