The influence of cigarette design on the content of phenols in mainstream tobacco smoke was studied. The most abundant phenols - catechol, hydroquinone, phenol, o-, m-, and p-cresol, and resorcinol - were determined by HPLC with fluorescence detection. Hydroquinone and catechol made the most significant contribution to the total content of phenols with maximum values of 135.0 µg/cig and 95.7 µg/cig, respectively. The highest total content of phenols (330.9 µg/cig) was measured in the smoke of a Virginia tobacco cigarette. The total content of phenols (µg/cig) in cigarette mainstream smoke decreased linearly with increased filter ventilation, R2 = 0.9536. The results obtained indicate that filtration and ventilation can strongly influence the mainstream tobacco smoke content of phenol and its less polar derivatives, o-, m-, and p-cresol, which were reduced by up to 85%. Hydroquinone and catechol are less affected and only cigarettes with the special “recessed charcoal filter system” and cigarettes with filter ventilation over 50% showed significant reductions. On a per mg ‘tar’ basis the largest contributor to phenols in cigarette mainstream smoke was the selection of the tobacco type. The use of any standard commercial filter on an unfiltered cigarette can substantially reduce the yield of phenols in cigarette mainstream smoke. The use of special filters (e.g., the “recessed charcoal filter system”) or high levels of cigarette ventilation does not reduce the amount of phenols in tobacco smoke considerably when normalized on a per mg ‘tar’ basis.