Background The consistency and the quality of medicine labels are sought through the regulatory frameworks. This study aims at investigating the secondary labels of medicines based on the labeling regulations and guidelines issued by the National Medicines Regulatory Authority (NMRA), Sri Lanka. Methods A descriptive cross-sectional study was conducted on 53 commonly used prescription-only oral medicines selected using the price regulations published for most commonly used drugs. High-resolution images of 216 brands/branded generics/generic products’ secondary labels were collected in April 2021 from six community pharmacies in six districts chosen as a convenience sample. Each label was manually assessed using a checklist prepared based on the regulatory requirements by four trained investigators. The status of registration of each product was assessed using the NMRA website. Descriptive statistics were performed. Results There was a variation observed in labeling regulations and information present on packages. Among the 216 products evaluated, only 148 (68%) products appeared as registered medicines on the NMRA website, and 2.3% of medicines fulfilled all stipulated labeling parameters set out by the NMRA, 3% of products abided by the general labeling requirements, and 76% of the products complied with labeling requirements for API. Major deficiencies were observed in the presentation of registration numbers and the details of the local agent, which were unaccounted for in 210 (97%) and 131 (61%) products, respectively. The highest consistency (100%) of information was noted with the dosage form, date of manufacture, date of expiry, and batch numbers. Among the restricted information, attractive pictures (2%), web addresses (6%), and over-stickers (34%) were found. Conclusions The results highlighted a gap between regulatory requirements and practice in medicine labeling information. Regular post-market examination of medicinal labels is highly advised in a country that relies largely on imports. Similarly, careful adherence to the labeling regulations is required. Furthermore, suppliers and local agents should be held accountable for ensuring accurate medicine labeling through increased awareness, education, and sanctions.