The circular waveguide aperture or open-end radiator, one of the canonical antenna elements, can be filled with a dielectric material for miniaturization. With dielectric filling, the aperture reflection increases and impedance matching is necessary. This paper presents a simple but innovative simulation-based approach to the aperture matching of a dielectric-filled circular waveguide aperture. By properly loading the aperture with two- or three-section dielectric rings, the impedance matching is possible over a wide frequency range starting slightly above the TE11-mode cutoff and continuing upward. The material for the aperture matching is the same as that filling the waveguide. The proposed matching structure is analyzed and optimized using a simulation tool for the dielectric constant εr of the filling material ranging from 1.8 to 10. For εr ≥ 5, the unmatched reflection coefficient ranges from −6.0 dB to −0.9 dB while the matched reflection coefficient is from −20.4 dB to −10.0 dB. The impedance matching has been achieved over more than an octave bandwidth.