<b><i>Aim:</i></b> This study aimed to characterize the clinical and pathologic presentation of ocular surface tumors (OSTs) and to more precisely differentiate the grades of ocular surface squamous neoplasia (OSSN) and benign lesions among Zambians. <b><i>Methods:</i></b> Two-hundred sixty-five Zambian patients presenting with ocular surface growths, suspicious for OSSN, were recruited between November 2017 and November 2019 to a cross-sectional study to investigate their lesions. Sociodemographic data were collected, HIV infection status and vision tests were performed, and lesions were measured and documented. Lesions >2 mm in diameter were excised and sent for pathology analysis. In addition to the biopsies, tears, blood, and buccal swabs were collected. CD4+ T-cell counts were measured by flow cytometry. Lesions were classified according to the WHO guidelines. χ<sup>2</sup> and bivariate correlations were used to analyze variable associations and strengths with phi/Cramer’s V and correlation coefficients, respectively. Binary logistics was used to adjust for covariance. <b><i>Results:</i></b> In this study, 68.3% of the participants were found to be HIV positive. The most frequent diagnoses were invasive OSSN (45.3%), preinvasive OSSN (29.1%), and pterygium (22.6%). Invasive OSSN comprised keratinizing squamous cell carcinoma (SCC) (87.5%), basaloid SCC (3.3%), and spindle cell carcinoma (3.3%). Unusual carcinomas, not described previously, included hybrid SCC (5.0%) and acantholytic SCC (0.8%). Invasive OSSN had advanced tumor (T3/T4) staging (93.3%) at diagnosis. Lymphadenopathy was rare (2.3%), and metastasis was absent. Patients were mostly female (59.2%). Median age was 36 (interquartile ranges 33–41) years (ranges 18–81). Patients with invasive OSSN were more likely to present with pain (<i>p</i> = 0.007), redness (<i>p</i> = 0.034), excessive tearing (<i>p</i> = 0.0001), discharge (<i>p</i> = 0.011), bleeding (<i>p</i> = 0.007), reduced vision (<i>p</i> = 0.0001), fungating lesion (<i>p</i> = 0.001), and blindness (<i>p</i> = 0.005); location at temporal limbus (<i>p</i> = 0.0001), inferior limbus (<i>p</i> = 0.0001), or circumlimbal (<i>p</i> = 0.001); and extension to cornea (<i>p</i> = 0.006) and forniceal palpebral conjunctiva (<i>p</i> = 0.001). Invasive OSSN was associated with any smoking habit and alcohol consumption (<i>p</i> = 0.04 and 0.03, respectively). HIV positivity was strongly associated with OSSN (74.6% OSSN vs. 49.3% benign lesions; <i>p</i> = 0.0001; phi: 0.237 [<i>p</i> = 0.0001]). <b><i>Conclusion:</i></b> OSTs are very common in Zambia and are strongly associated with HIV coinfection. Patients with OSSN were more likely to be HIV positive than those with pterygia. Despite the commonality of OSTs in sub-Saharan Africa, these cancers have historically been poorly characterized.