The garment industry contributes enormously to the socio-economic development of societies. Inadequate facilities compel small-scale workers to carry out most of the garment production processes manually during long working hours, thereby affecting their health. Repetitive activities such as patternmaking and assembling have their own health challenges. The study envisages health-related problems involved in garment production processes and their effects on the wellbeing of tailors and dressmakers. To help achieve this, the research examines the workplace health and safety compliance situation in the small-scale garment industry and identifies health-related problems associated with production processes. A qualitative research approach was employed. The population for the study comprised tailors and dressmakers who have consecutively been in the garment production sector for a period of five to twenty years. A snowball sampling technique was used to gather a sample of forty (40) dressmakers and tailors. In-depth interviews with structural questions, observation, and focus group discussions constituted the data collection instruments. The study reveals that the knowledge level of tailors and dressmakers with respect to health issues is very low. Again, the research identified the use of unprescribed medications for the treatment of waist pain and headaches. This research highly recommends government and stakeholders' interventions to help improve the welfare of tailors and dressmakers working in the small-scale garment industries.