Speciality choice is an important decision for doctors, often starting during medical school. In Nigeria, where the doctor-to-population ratio is low and worsened by emigration, understanding medical students' speciality preferences can inform strategies to ensure a balanced distribution of specialists. A total of 500 pre-tested semi-structured questionnaire were distributed among medical students at Obafemi Awolowo University of which only 350 full and suitable responses were retrieved. Data were analysed with SPSS 26, and chi-square test of significance using a confidence interval of 95% was done with p value of less than 0.05 considered statistically significant. The most preferred specialities were surgical (101; 28.9%) and medical (68; 19.4%), while community medicine (9; 2.6%) and laboratory medicine (4; 1.1%) were least preferred. A significant number (124; 35.4%) of students remained undecided, particularly among lower-year students. Gender influenced choices, with males favouring surgery and females leaning towards paediatrics. There was statistical relationship between gender and speciality choice at 95% confidence interval (p = 0.0002 < 0.05, x[superscript 2] = 26.26, df = 6). Key factors influencing speciality choice included personal interest, abilities, and perceived competence. The prestige associated with surgery attracted males, while females preferred specialities offering better work-life balance, such as paediatrics. This study recommends the need to revise the medical curriculum to encourage interest in underrepresented specialities like community and laboratory medicine.