The Headmaster’s Lodge, along with the main school building containing classrooms, six dormitories, a small library, quarters for five masters, Chapel of the Holy Trinity, a hospital and quarters for the Sergeant and Matron were erected by Major Innes RE, on a plan furnished by Crawford Campbell Esq, CE. They were built in 1866 in the Gothic style at a cost of Rs.1,74,954.30, less cost of the Chapel and levelling of the “first” and “second” flats.
The first Headmaster Rev. Samuel Slater, who so successfully started and established the school, was the first resident of the lodge.
Customarily, all Headmasters have used the ground floor. The first floor was initially used for “parlour boarders" and at one time the junior library, and Old Cottonians rooms. Currently, conference hall and three guest rooms are located on the first floor.
Growing within the gardens of the Headmasters Lodge is the only English Oak of its kind in all of Shimla. The Himalayan elm, the largest of all trees on the 56 acre school campus, stands on the edge the Lodge and over the Headmaster’s office is older than the school – a towering guardian of traditions.
| Head Master | Year | To |
| The Rev. S. Slater D.D. | 1863 | 1885 |
| The Rev. H.M. Robinson | 1885 | 1886 |
| The Rev. E.A. Iron MA | 1887 | 1901 |
| The Rev. H.M. Lewis MA | 1901 | 1918 |
| The Rev. R.R. Gillespy | 1919 | 1922 |
| The Rev. W.S. O'Neil MA | 1923 | 1926 |
| The Rev. J.R. Peacy MA, MC | 1927 | 1935 |
| The Rev. Canon G. Sinker MA | 1935 | 1945 |
| The Rev. F.M. Drake BA, BT | 1946 | 1949 |
| Mr. F.H. Fisher BA, BT | 1949 | 1953 |
| Mr. E.G. Carter OBE, MA | 1956 | 1957 |
| Dr. T.M. Dustan, MA, BD, DD | 1958 | 1962 |
| Major R.K. Von Goldstein MBE, MA | 1963 | 1976 |
| Brig. S.J. Mukand MA LT, DP Ed | 1976 | 1986 |
| Mr. R.N. Hakim MA LT | 1986 | 1993 |
| Mr. Kabri Mustafi MA, B.Ed | 1994 | 2004 |
| Mr. Roy Christopher Robinson M.A, B.Ed, T.T.CÂ | 2004 |
