Background: Proactive behaviour, triggered by various individual and/or contextual antecedents, could be a significant added value to cope with the major challenges midwifery students face in adapting quickly and effectively to different clinical settings. Aim: Assessing the presence of various individual and contextual antecedents in a group of midwifery students and explore their association with proactive behaviour which could bring benefits to the constantly evolving field of reproductive healthcare. Methods: A cross-sectional study was conducted to investigate associated antecedents of proactive behaviour in a group of midwifery students (n = 421) between December 2017 and February 2018. Findings: More than half (66.8%) of the midwifery students demonstrated some kind of proactive behaviour. Albeit, 13.6% of the proactive behaviour was associated to the appearance of the investigated individual and/or contextual antecedents. The Dutch nationality, the evolution in the educational programme, a high role breadth self-efficacy, generalized compliance, trust in peers and autonomy were all positively associated to proactive behaviour. Conclusions: Midwifery students showing generalized compliance to the organization, have a high role breadth self-efficacy and trust in their peers are positively associated to proactive behaviour. Discussion: Anticipating the various significant antecedents during the midwifery education, could strengthen the level of proactive behaviour of future midwives. The awareness of for proactive behaviour could have a positive contribution to the work efficiency and coping attitude of future midwives. This will indirectly contribute to the quality of care for mother and child.