A two-year (2010 and 2011) open field experiment was conducted to study the effect of drip irrigation and seasonal variation on the yield parameters and main bioactive components, carotenoids (mainly all trans, cis lycopene, and β-carotene), polyphenols (chlorogenic acid, caffeic acid, gallic acid, quercetin, rutin, naringin, etc.), and tocopherols of processing Strombolino F1 cherry tomatoes. The irrigated plants (STI) gave a higher marketable yield (61% and 101% respectively), and rain fed plants showed a yield loss. Water supply had a strong positive (R2=0.98) effect on marketable yield in 2011, but weak (R2=0.69) in 2010. In both years, the antioxidant concentration (all carotenoids, total polyphenols, tocopherols) showed a decrease with irrigation. Water supply affected the composition of carotenoids to a considerable extent. The optimum water supply treatment gave a lower proportion of lycopene than the rain fed control (STC) treatment. We observed significant negative correlation between rutin concentration and irrigation. The α-tocopherol concentration was significantly higher in STC treatments. Irrigation negatively influenced antioxidant concentrations of cherry tomato fruits, but higher yield could account for the concentration loss of individual fruits by higher antioxidant production per unit area.