The main characteristics of high-efficiency switching-mode solid-state power amplifiers with envelope elimination and restoration (EER) methods depend on all their elements. In this article, we study the influence of the types and parameters of the envelope path low-pass filters (LPFs) on the EER transmitter out-of-band emissions. This article presents for the first time an analysis of EER transmitter operation where the output impedance of the PWM modulator is not equal to zero, as usual (with a one-sided loaded LPF), but is matched with the low-pass filter and the load (with a double-sided loaded LPF). Theoretical comparisons of EER transmitters’ out-of-band emissions were carried out with four envelope path LPF configurations (one-sided and double-sided loaded LPFs with a smooth and sharp transition, respectively), for both the nominal load (broadband antenna) and resonant antennas with a limited bandwidth. The analysis showed that for the case of transmitter operation on a resonant antenna with a limited bandwidth, the preferable option was the use of a sixth-order double-sided loaded LPF with a smooth transition. The use of the proposed modulator configuration allowed the transmitter to operate on an antenna with VSWR = 1.07 at the edges of the transmitted signal band with a minimum LPF bandwidth equal to 5.8 bands of the amplified signal. This could significantly expand its application capabilities and allow one to reduce the PWM clock frequency and increase efficiency.