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<i>Background and Objectives</i>: A prospective, randomized clinical trial was conducted to evaluate the concentration of ofloxacin in the aqueous humour (AqH) of patients suffering from dry eye disease (DED) after topical instillation. <i>Materials and Methods</i>: Ninety-one (91) cataract patients scheduled for phacoemulsification were categorized into three groups according to DED severity. Group I (<i>n</i> = 17) was comprised of subjects without DED, patients in group II (<i>n</i> = 37) were evaluated as having non-severe DED, while group III (<i>n</i> = 37) consisted of patients suffering from severe DED. Preoperatively, patients received 4 drops of 0.3% of ofloxacin at 15 min intervals. One hour after the last instillation, aqueous samples were collected intraoperatively. <i>Results</i>: The median AqH concentration of ofloxacin in group I was 199.9 ng/mL (range 92.2–442.8 ng/mL), while in group II it was 530.5 ng/mL (range 283.7–1004.9 ng/mL), and 719.2 ng/mL (range 358.0–1512.4 ng/mL) in Group III, <i>p</i> < 0.001 (Kruskal-Wallis tests). Pairwise tests (two-tailed with Bonferroni corrections) between groups resulted in a <i>p</i>-value of 0.001 when group II was compared to group I and group III was compared to group I, and a <i>p</i>-value of 0.020 when group II was compared to group III. The severity of DED, across groups I, II, and III, and the levels of ofloxacin revealed a strong positive correlation (r = 0.639, <i>p</i> < 0.001). <i>Conclusions</i>: Ofloxacin concentration in the AqH after topical drop instillation may be affected by the degree of ocular surface inflammation in patients suffering from DED.