Current computer systems require communication between integrated circuits through a printed circuit board at increasingly higher clock frequencies. A major issue for reliable transmission of such high-speed digital signals is the losses, which increase with frequency. Due to the conductor and dielectric losses, the amplitude of a transmitted signal starts decreasing as it propagates from the driver to the receiver. If the amplitude falls down a threshold value, the receiver may not be able to differentiate it from a noise signal. In this thesis, a methodology will be developed to extract the dielectric constant and loss tangent of PCB dielectrics for printed circuit boards, parallel-plate waveguide structures will be designed and measured. These structures resemble a parallel-plate capacitor that resonates at higher frequencies. A simulator will be developed to analyze these structures based on 2D discrete cosine transform. Simulation results will be compared with measured data to extract the dielectric constant and loss tangent.