Speech intelligibility (SI) tests under realistic acoustic scenarios are complex tasks to perform. Optimal acoustics, in terms of reverberation and noise, are thus needed. This is particularly true in the presence of young hard-of-hearing (HoH) children equipped with cochlear implants who need speech to be highly intelligible to learn. During the COVID-19 pandemic starting in early 2020, wearing face masks became common to avoid the spread of infection, mainly impacting the increasingly challenging task of listening for HoH listeners. This study investigated the influence of different types of face masks on speech intelligibility and listening difficulty under competitive noise scenarios. Fourteen children with cochlear implants were involved, as well as six children with typical hearing. Three types of face masks with different acoustic, filtration, and breathability characteristics were considered; three signal-to-noise ratios (SNR) of +10 dB, +5 dB, and 0 dB were used. As expected, lower SNRs corresponded to lower speech intelligibility, and SI without a mask was similar to that obtained with a mask at the lowest acoustic attenuation, albeit with a low filtration efficiency. These preliminary outcomes help improve speech communication strategies in classrooms to support optimal listening conditions.