The role of the pharmacist or pharmaceutical technologist is to scrutinize errors in the prescription made and make appropriate recommendations/interventions to the prescriber if any. In many countries, including Kenya, Nigeria and India, drug retailers prescribe and sell medicines over-the-counter. The WHO advocates that rational dispensing principles should be followed at all times to ensure that patients receive adequate information regarding the use of dispensed medicines, so as to achieve the desired benefits. The objective of the study was to undertake an evaluation dispensing prescription antibiotics at the community pharmacy outlets. A descriptive cross sectional study design was used by the study. A sample size of 196 was calculated using Fisher’s formula. Stratified random sampling (nth of 10) was used to select community pharmacy outlets within Mombasa town. Simple random sampling was used to recruit the subjects into the study by assigning natural numbers to all prescriptions with an antibiotic during the study period. . A well designed checklist developed to capture study variables was used to collect data from the prescriptions as well as three interviews were carried out among the patients and pharmacists. The collected data was edited and transcribed before entered into SPSS version 21 for analysis and interpreted using tables, pie charts and graphs. The study findings show that the patient (89.3%) and prescribers name and address (83.7%) were well captured followed by prescriber signature (75.3%), safe dosing (75.5%), prescription date (63.3%), cautionary information (62.2%) and stamp (38.5%). Bivariate analysis findings show that all prescription legality or validity parameters were statistically significant. The study recommends that the prescribers should always adhere to prescribing guidelines, embrace the legality of prescriptions on appropriate diagnosis, appropriate drug and appropriate patient in order to limit any likelihood of drug misuse or abuse. The pharmacists and pharmaceutical technologists should always not assume provided their patients with neat, clear and elaborate drug labels because it can reduce any likely mistakes and promote appropriate drug use