The Revd. W. R. B. Kuye took over the Principalship of the school on 24th January, 1922 and held the post till December, 1931 when he left to become curate of St. Paul’s (Breadfruit) Church, Lagos. A strict disciplinarian and an accomplished musician, the Revd. W. R. B. Kuye strove hard to maintain the high standard of discipline which the school had attained. To him, the Abeokuta Grammar School was ‘that magnificent oven’ that was meant to bake highly disciplined and accomplished students that would play significant roles in the life of their country. It was during the tenure of the Revd. W.R.B. Kuye that some of the anthems that have since entered the repertoire of the school were learnt. He also infested many of the students that passed through his hands with his love of music.

Revd. I. O. Ransome-Kuti came over from ljebu-Ode Grammar School in February 1932 to assume the Principalship of Abeokuta Grammar School. He held the post till 1954 and has the distinction of being the longest-serving Principal of the School so far. The Revd. I. O. Ransome-Kuti scored a few other ‘distinctions’ as far as the Abeokuta Grammar School is concerned. He was the first student to be enrolled in the Admission Register of the School. This earned him the title of ‘DAWODU’ of the School – ‘DAO’ for short; He was the first old boy of the school to serve as a substantive Principal of the school, Messrs. E. A. Kasumu (later, Chief E. Adegunle Soetan) and C. B. Kuforiji being Acting-Principals. The new Principal threw himself whole-heartedly into the job of raising further the standard of the school and inculcating in his students values that would make them exemplary citizens. In one of the speeches made during the Silver Jubilee Celebrations of the School in 1933 the then Alake, Oba Ladapo Ademola II, had this to say of him: “It is no flattery or hyperbole when I say that the Abeokuta Grammar School must congratulate itself for having as its Principal today a very energetic and conscientious worker as the Revd. I. O. Ransome Kuti; he is just the right man in the right post… I have implicit confidence in him, his ability and the way and manner he has efficiently improved the school since he took over the charge is a sure proof that I am right to do so…” It is common knowledge that the school blossomed under Principalship of the Revd. I. O. Ransome – Kuti. Apart from enriching the curriculum of the school, enhancing its academic performance, and improving its tone, he also took keen interest in beautifying the surroundings of the school. He laid out the beautiful lawns of the lgbein site with their paths, hedges, and beautiful flowers. He completed the construction of the school field through the labour of the students, by levelling the mound at the eastern end of the Main building – and that at a time when caterpillars and other earth-moving equipment were unknown. He extended school land through purchases, built more classrooms, introduced the teaching of science and technical subjects, games and sports. Above everything else he trained his students to value honesty and the development of strong character and to relish hard work. It is pertinent to note that to ensure a constant supply of teachers of the right caliber who would help in ensuring the maintenance of the best traditions of the school and their transmission to generations of students the Revd. I. O. Ransome-Kuti began the system of sponsoring old students of the school in institutions of higher learning for the specific purpose of returning to teach in their Alma Mater. Between 1943 and 1945, the Revd. I.O. Ransome-Kuti served on the Elliot Commission whose report led to the founding of the University College, Ibadan (now, University of Ibadan). In his absence, the Senior Tutor, the late Mr. H. F. A. Kuforiji (alias ‘Oxy’), himself an old boy, acted as Principal of the school.

The Revd (now Rt. Revd) J. S. Adeniyi (Rtd) took over as Principal in January, Good 1955 and built on the foundation so ably laid by the Revd. I. O. Ransome-Kuti. Revd. J. S. Adeniyi added to the facilities on the lgbein site by building Staff Quarters, the Principal’s Quarters, and the imposing Science Block which also housed the School Library and Sixth Form Lecture rooms. It was during his tenure also that the Higher School Certificate was introduced into the school. It was also during Revd. J. S. Adeniyi’s tenure that expatriate teachers began to be re-invited to teach in the school. The first of such teachers was Mr. David J. Henwood, a great mathematician of note. Others came from Britain, United States of America, and Asia. There was also the South African, Mr. (later Revd.) D. T. Matebese. Furthermore, it was during the period of Revd. Adeniyi’s Principalship that the extensive piece of land at Idi Aba which is now the permanent site of the school was bought. He also erected on it the first building a block of 10 classrooms, which was used by Classes I and Il for many years before the whole school eventually moved to ldi Aba. The original idea behind the purchase of the ldi Aba site was to relieve the congestion on the (old) Igbein site by stationing a section of the school there. When the Revd. J. S. Adeniyi was away to Great Britain and the United States of America in 1958, Mr. Femi Oyewole, an-other old boy, acted as Principal of the School.

Mr. H. O. Odedairo, an old boy of the school and the first layman to be a substantive Principal of the school succeeded the Revd. J. S. Adeniyi in May, 1967 and headed the School till January, 1975. He did his best to enhance the academic standard of the school and to continue the development of the new site. During his tenure the technical subjects block otherwise known as the I. D. A. building was built on the new site and the teaching of Technical Drawing was vigorously pursued. It was in his time that the subject was first offered at the School Certificate Examination. He also erected a block of four laboratories on the new site to serve originally as junior laboratories. They are now used as Chemistry arid Biology Laboratories – two laboratories for each subjects. The Diamond Jubilee of the School was celebrated during Mr. Odedairo’s tenure.

Mr. (later Chief) A. A. Akinyanmi took over from Mr. Odedairo in February, 1975 and headed the school till August, 1976. During his tenure he strove hard to curb the activities of land encroachment by land speculators on the (old) Igbein site.

Revd. J. A. Adenuga, took over from Mr A. A. Akinyanmi and headed the school till 31st August, 1977. It was during his tenure that the school had to move wholesale hurriedly in 1976 to the new site to make way for the Federal Advanced Teachers College which was to occupy the lgbein site as its temporary site. The College has since been renamed the Federal College of Education and has moved to its permanent site at Osiele. The Revd. J. A Adenuga had the difficult task of running the school from three different locations while his office was at lgbein. the Boarders were accommodated in part of the premises and buildings of the Trinity Nursery and Primary School at ljaiye, some classes were billeted on the grounds of the Baptist Women’s Teachers Training College, Idi Aba and cordoned off with fencing wire while the rest of the school occupied the new site at Idi Aba using every available space – wooden shack, the unfurnished Science Block and, of course, the oldest block on the site, the 10 classrooms Block.

Mr. F. O. Oridota, another old boy of the school, took over on 1st September, 1977 and headed the school till 31st December, 1986. It was left to him to complete the process of resettlement on the new site. The students on the premises of the Baptist Women Teachers Training College were found classroom accommodation on the new site while the female boarders were housed temporarily in the Administrative Block under the supervision of a Housemistress, Miss N. Obeng-Addae, (later Mrs. N. Somolu and Principal of Baptist Girls High School Idi Aba). The School office still remained at lgbein. Efforts were made to provide the school with a sporting field and Inter-House Sports Competitions had begun to be held on the School’s grounds. Furthermore, efforts were also made to sow and nurture on the new site the seeds of all that is best in the traditions that have made the old students continuously proud of their Aima Mater.  

Chief Israel Olufemi Akiyode, another old student of the School succeeded Mr. Oridota on 1st January, 1987. Chief J. O. Akiyode continued to keep the flag flying and addressed himself to consolidation of the physical development of the school and the upholding of the enviable ideals for which the school is noted.

Mr. D. A. Okunade became the principal in 1992 and served till 1995. In his era the school became famous in the Jyunior Engineers, Technicians and Scientists (JESTS) Programme, where the school won state and national laurels.

Mr. (later Chief) Olufunso Olayiwola Ogun became the principal in 1995 and served till 2012. A number of landmark achievements were recorded during his tenure. It was while he was at Abeokuta Grammar School the state government mooted the idea of Principals General. He happened to be one of the first three appointed by the then state government.