Oleocellosis or oil spotting on the peel of citrus fruit is a common post-harvest injury caused by improper handling. Mechanical injury allows phytotoxic oil to leak out of oil glands and cause injury to surrounding flavedo cells, resulting in oleocellosis. Mechanical harvesting (MH) of 'Valencia' sweet orange is conducted in late spring, when the next season's fruitlets are in their early stages of development. There is a concern that mechanical injury from harvesting machines can cause oleocellosis and fruit drop of young, green 'Valencia' sweet orange fruitlets, especially late in the harvest season when fruitlets are relatively large. We evaluated the effects of winter drought stress and subsequent late-season MH with a canopy shaker on oleocellosis of 'Valencia' sweet orange fruitlets. In April, mature fruit size, juice content, total soluble solids, and acidity were unaffected by previous winter drought stress treatments. Mechanical harvesting removed ~90% to 95% of mature fruit and 20% to 50% of fruitlets depending on previous drought stress treatments and harvesting date. Beginning 1 week after the late harvest (13 June), attached fruitlets were tagged and visually evaluated approximately every other month to determine oleocellosis injury until the late-season harvest 12 months later. Only 12% of the fruitlets had oleocellosis on more than 30% of their surface area. Up to 75% of the fruitlets from the previously drought-stressed trees had less than 10% of their surface area injured after MH and 11% of these fruitlets dropped before harvest. Nonetheless, there was no significant increase in fruit drop with increased surface area injured nor was juice quality affected at harvest. Overall, fruit surface oleocellosis decreased and healed as fruit expanded, but surface blemishes did not completely disappear. Thus, fruitlet oleocellosis in late-season mechanically harvested trees was cosmetic and did not increase fruit drop nor alter internal fruit quality.