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The need for a boarding house for St. John’s was felt in 1889. The first boarding house was erected with the funds collected from Old Boys to perpetuate the memory of Mr. Evarts, on the additional piece of land which was bought in 1876 by the Rev.D.Wood.
During October 1901, three of the four wings of the boarding-house were also ready to use. In 1904 the final wing of the boarding-house was built.
The boarders organized the Boarders’ Union in September 1909. This was carried out by forming six committees to direct the activities of the members – Literary, the Social, the Athletic, the Garden, the Sunday-school, and the Scripture Union Committees.

The proceeds of the sale of a piece of a land gifted by Dr.J.M.Handy were used for the erection of a new dormitory for the senior boarders built in honor of the Rev.G.T.Fleming, the Principal of the College from 1880 to 1889. In 1920, the Thompson Boarding House, so called in memory of the Rev.Jacob Thompson’s long Principalship, was purchased. This enabled the College boarders to be divided into three distinct grades, the senior, intermediates, and juniors. During 1942, the Principal introduced the noble idea of the Cottage System of boarding houses. In this, the boarding house master and his family were given quarters adjoining the boarding houses so that they and the boarders lived as members of one family.

In 1953, Crossett Memorial building fund was launched for the construction of a hostel. Dr. & Mrs. Rajasingham gifted Rs 30,000/= towards this building fund. Dr.Rajasingham was a distinguished Old Boy and his gift was the biggest the college had received. It was decided to name part of the new hostel as the Rajasingham Block and another part as the Crossette Block. As more funds were required for this purpose, the College had Science Exhibition and Fairs in 1953, 1955 & 1957.
In 1954, Mahendra Theatre, sited opposite the College was purchased which was funded by Old Boys. This was converted into a hostel and named Henry Peto Hostel, thus fulfilling one of the main resolutions adopted by the Old Boys at the Jubilee Celebrations. This was ceremonially opened by Mr.C.Suntharalingam.

In 1955, the new hostel was opened by the Bishop of Colombo on 24th June, 1955. It was named the Memorial Block. It had four wings, one was named in memory of Dr.A.Rajasingham, another named in memory of his son Alison Rajasingham, his only child who had died fairly young, the third wings was named in memory of Mr.T.H.Crossette and the fourth wing named in memory of Rev.C.C.Handy. This block had all modern amenities with four rooms, three for boarding masters and one for the Senior prefect.
The Foundation stone for the Rao Sahib James Chelvanayagam Chinnappa Block for Hostel, Gymnasium, Health Centre and Classrooms for instrumental music was laid by Ven.S.P.Nesakumar, Archdeacon of Jaffna and Manager of the College, on Saturday 19th March 2011. This block was dedicated to the glory of God and the spread of knowledge by the Rt.Rev.Dhiloraj Ranjit Canagasabey, 15th Bishop of Colombo, and declared open by Mrs. Harshini Canagasabey on Wednesday 7th March 2012.

It was the vision of Dr. (Mrs.).Malathi Rajasingham along with other Old Boys of the school and well-wishers that made possible for the construction of this building. St John’s is grateful for the generous support of Rs 10.82M, by the members of Dr.Malathi & Arjuna Rajasingham family towards the construction of Arjuna Bartlett Rajasingham Hostel, James Chandrasekaran Virasinghe Chinnappa Hostel, and Lucia Navamani Virasinghe Chinnappa Chapel that are housed in the Rao Sahib James Chelvanaygam Chinnappa Hostel Block.
James Chelvanaygam Chinnappa was a student of our college and later upon graduation from Presidency College came back to teach Mathematics at our college until June 1908, when he went to Madras to further his career as an educationalist and teacher. He lectured in Philosophy and Mathematics at the Presidency College and later helped lead the Education Department of the Madras Presidency as its Deputy Director of Public Instruction. He was decorated by India with the title of Rao Sahib before his death in 1937.