During its founding years between 1930 and 1934, Madrasah Al-Arabiah Al-Islamiah (MAI) operated in a small building located beside Haji Yusoff Mosque at Hillside Drive. It was believed that MAI also used another room within Haji Yusoff Mosque for its activities.
The madrasah served residents in the Serangoon area, and admitted up to 40 students during that period. The religious teachers and volunteers taught mainly Islamic Religious Knowledge, Arabic and Qur’an Reading.
In 1965, as the physical state of the madrasah building was in a poor condition, a Madrasah Management Committee was formed to raise funds for rebuilding. By 1970, the committee had only managed to raise a little over $3,000, way below the target sum of $30,000. However, the madrasah persevered to continue serving the community in the area.
“Tujuannya untok membena samula sekolah yang samakin uzur keadaan-nya... Wang yang telah dikumpulkan... melalui kelebehan kutipan zakat fitrah, jualan buku, derma persaorangan dan lain2-nya.”
– How the community raised funds to rebuild the madrasah
‘J-kuasa akan tentukan NASIB tabong madrasah’, Berita Harian, 13 September 1970
Unfortunately, on 26 July 1982, a fire broke out due to an electrical wiring fault. The madrasah was burnt down. After the fire, only 17 students returned, with lessons resuming within the Haji Yusoff Mosque. Students sat cross-legged on the floor to study alongside their teachers. Without a proper building, functioning classrooms and facilities, the student population dwindled further. In a September 1982 Berita Harian article, it was estimated that $30,000 would be required to rebuild the madrasah.
In 1989, MAI eventually came under the management of the Muhammadiyah Association. At that time, Muhammadiyah Association had already established its own madrasah, Madrasah Ulumul Quran (MUQ) which was in its third year of operation. MUQ already had about 100 primary school students then. The two entities merged. The name Madrasah Al-Arabiah Al-Islamiah was retained and Muhammadiyah Association operated both primary and secondary levels, with its inaugural batch of ‘O’ level students in 1998.
 ‘Pelajar madrasah Al-Arabiah terus belajar di Masjid Haji Yusof’, Berita Harian, 8 September 1982
In late 2003, Majlis Ugama Islam Singapura (Muis) introduced the Joint Madrasah System (JMS). Its aim is to assist the madrasah sector to upgrade and put in place systems that would best fulfil their mission of producing asatizah (religious teachers), Islamic scholars as well as quality graduates who could contribute to the Singaporean Muslim community.
In 2007, three madrasah signed a Memorandum of Understanding (MOU) to be part of the JMS: Madrasah Irsyad Zuhri Al-Islamiah, Madrasah Aljunied Al-Islamiah and Madrasah Al-Arabiah Al-Islamiah (MAI).
MAI positioned itself as an academic secondary school with a niche in science programmes, conducted in an Islamic environment. It ceased its intake of Primary One students in 2009.
MAI students will take their first ‘O’ level examinations in 2018 under the JMS.
In 2016, Dr Yaacob announced that MAI will be getting a new building next to the current temporary location in Toa Payoh, projected in Jan 2020.