To investigate the relationship between chemotherapy-induced lacrimal drainage (LD) obstruction and obstructive meibomian gland dysfunction. Twenty patients who had received chemotherapy were divided into 2 groups, according to the presence of LD obstruction: the LD obstruction group (n = 10) and control group (n = 10). Upper and lower meibomian gland loss was evaluated using noncontact meibography, and tear film lipid layer thickness was measured using an interferometer. The mean values of the right and left eyes of each patient were used to compare parameters between both groups. The LD obstruction group had higher levels of meibomian gland loss in both upper (42.9% ± 16.4%) and lower meibomian glands (80.1% ± 16.7%) than did the control group (17.3% ± 6.7% and 22.8% ± 13.0%, respectively) (P < 0.001 and P < 0.001, respectively). In the LD obstruction group, meibomian gland loss in the lower eyelid was significantly higher than that in the upper eyelid (P < 0.001). The lipid layer was significantly thinner in the LD obstruction group (28.4 ± 9.7 nm) than it was in the control group (72.9 ± 22.5 nm) (P < 0.001). Patients with chemotherapy-induced LD obstruction had greater meibomian gland loss and thinner lipid layers than did patients without LD obstruction. Chemotherapeutic agents that induce LD obstruction can also block the meibomian gland orifice, resulting in obstructive meibomian gland dysfunction through the same mechanism.