Most women perceive labour pain and childbirth as the most severe and agonizing event in a woman’s life. Midwives play critical role in supporting women through the painful birthing process, to the desired favourable outcomes for mother and baby. The primary objective of this study is to evaluate the practices and challenges of pain management during the initial stage of labour among midwives at the University of Medical Sciences Teaching Hospital Complex in Akure. From July to October 2021, a facility-based descriptive cross-sectional study was conducted with 72 midwives employed at the University of Medical Sciences Teaching Hospital Complex in Akure. The first stage of labour pain management practices and challenges were evaluated among the study participants using a questionnaire. SPSS (version 23.0) was used in processing the data. In the first stage of labour, environmental pain management approach was shown to be the most used (95.4%), followed by psychospiritual pain management approach (91%); while the least employed was the pharmacological approach (63.4%). Effectiveness of the approaches were perceived to be in the following order: psychospiritual, environmental, physical, pharmacological and social. Lack of resources (84.7%) and understaffing (33.3%) were cited as part of the challenges associated with pain management. It is important for the government to provide adequate staff, equipment and conducive birthing environments; while the midwives continually educate patients on available non-pharmacological and pharmacological labour pain management approaches during their prenatal care visits, to enhance their self-efficacy and cooperation in labour.