Al-Qiwamah is a Qur’anic concept that maintains the accountability of man to protect and supervise the affairs of woman. The Qur’an explicitly indicates that “men are caretakers of women” (4:34). The concept has been considered contentious by many, particularly considering its remarkable focus on the creation of a male-centric social structure. A number of critiques also believes that the doctrine works as a basis of misogyny within the Qur’anic worldview. There is a void of adequate academic attention on the approach of exegetes of the Qur’an in dealing with the doctrine of al- Qiwamah. With this background, the present research attempts to evaluate the viewpoints of prominent exegetes of the Qur’an on the doctrine of al-Qiwamah as well as to compare the point of views on between classical and contemporary scholars. Accordingly, the researcher has cautiously selected five exegetes from each the classical and modern periods, namely, al-Ṭabari, al-Razi, al-Zamakhshari, al-Qurṭubi and Ibn Khathir from the classical scholars; Rashid Riḍa, Sayyid Qutb, Ibn 'Ashur, Mawdudi and Sha'rawi from the modern Qur’an scholarship. In order to achieve this, the procedure employed is a combination of different research methods, namely, inductive, analytic, comparative and critical. The study suggests that, a gradual development in the meanings of the doctrine of al-Qiwamah is evident within the tafsir collections. Compared to the medieval exegetes, modern mufassirun were more vigilant against the feminist discourses and the accusations of misogyny. However, it is pertinent to note that none of the exegetes, neither classical nor the modern, considered al-Qiwāmah as a tool of male oppression. The study also reveals that according to the entire collections of Qur’anic exegesis, al-Qiwamah represents the construction of a social structure intended at attaining twofolded objectives of the Quranic worldview: to uphold an ideal system of familial institution on the basis of biologically balanced gender roles and to ensure the ultimate result of protection of woman. In examining a highly significant area of Qur’anic studies, the study is expected to be a valuable contribution to the discourse on al-Qiwamah, as well as its remarkable addition to the discussions of gender roles in Islam.