Ophthalmological examination requires a strict contact between caregivers and patients. In the COVID-19 era, this may be a risk factor for virus spread, and the use of facial masks for all in-office ophthalmological procedures has been recommended. In this case-series, we report about some errors in intraocular pressure measurement, that may occur during the slit-lamp examination of patients wearing filtering facepiece masks and N95 respirators. This is mainly due to the greater dimensions of these masks in comparison with the surgical standard ones, and to the presence of a preshaped rigid nose area that may press against the Goldmann tonometer. Special care should be taken when measuring intraocular pressure in these cases.