The introduction of Islam to Indonesia necessitated the dissemination of knowledge regarding the Quran and its interpretation. Historical records indicate that in the 17th century CE, Sheikh Al-Fansuri authored a Malay-language Quranic exegesis titled Tarjuman Al-Mustafid. Later, in the 19th century CE, Sheikh Muhammad Hasbi Assiddiqi made significant contributions by writing a Quranic interpretation known as Tafsir Al-Majid An-Nur. Notably, both scholars hailed from the same region of Indonesia, Aceh. This research aims to examine the methodologies employed by these two scholars—Al-Fansuri and Assiddiqi— in addressing modern interpretative issues such as al-Mathur (transmitted traditions), Ra'y (opinion), Isra'iliyat (Israeli traditions), Ilmi (scientific), Bayani (rhetorical), and Lughawi (linguistic). Furthermore, the study explores their positions on gender-related matters, such as polygamy, women's participation in politics and work, and women's attire. The research employs an inductive approach to gather all relevant information concerning the interpretative methodologies of Al-Fansuri and Assiddiqi, as well as their views on women's issues. A comparative approach is used to analyze their interpretation methods and stances on the aforementioned topics. Finally, an analytical approach is adopted to critically discuss the findings, examining the scholars' positions on interpretation and women's logically and scientifically. The research concludes several findings, including that both scholars utilized similar methods in their interpretations, such as al-Mathur, Ra'y, Bayani, Lughawi, Fiqh (juridical), and Ilmi approaches. However, Sheikh Assiddiqi's stance on women's issues appears more stringent and explicit than Al-Fansuri’s. This discrepancy can be attributed to the different social and cultural contexts in which the scholars lived, with the needs and concerns of Assiddiqi's time influencing his more rigid positions on these matters, in contrast to the more flexible approach found in Al-Fansuri's work.