W. S. Gunawardena (first principal 1876–1891)

W. S. Gunawardena (B.A. Calcutta) was the first principal and served from 1876 until 1891. The school hostel was started in 1882 and cricket was also introduced to the school during this period.^[12]

Philip Lewis (principal 1892–1896)

Philip Lewis became the second principal and served from 1892 until 1896. Although there were many difficulties, a rapid development of the school could be seen during this period.

J. G. C. Mendis (principal 1896–1917)

J. G. C. Mendis (B.A. Cambridge), the son-in-law of the founding patron, rendered a valuable service to the school for two decades, from 1896 to 1917.^[13][14] During his tenure a school cricket society was formed and the school ground was further developed.^[12] The school magazine: The Cambrian (first issued in 1897), the debating team, cadet corps (1903), library, laboratory, commerce section, tennis and soccer teams, and a children's park were some of the elements added to the school during this era. Another important milestone was the formation of the Old Boys’ Association in 1904. After 21 years of service, Mendis had to retire from his post as principal due to deteriorating health.

P. T. Jayasuriya (principal 1917–1925)

P. T. Jayasuriya [B.A. Hon.(Lond)] became Mendis' successor as principal. During his time at the school, the academic aspect of the school improved significantly, with students obtaining great results. Under Jayasuriya, the science section and the school cricket ground were developed further and a separate children's park for the school was built. In 1922, The Cambrian was published again and the infrastructure of the school was also enhanced by the addition of three more classrooms. A house system was initiated and four houses were named, after the founder and the first three of the principals: namely, Founder's, Gunawardena, Lewis, and Mendis.

L. E. Blaze (principal 1926)

In 1926, Louis Edmund Blaze (B.A. Cantab) was appointed principal. He was the founder of Kingswood college, Kandy, a former student of Trinity College, Kandy and the father of school rugby football in Sri Lanka. He was a very dynamic person and the "Golden Jubilee Prize Giving" was held during his period. The English College anthem was also written during this period.

L. G. Crease (principal 1927–1931)

L. G. Crease (M.A. Oxen) headed the school from 1927 to 1931. He was from Europe and was very strict when it came to student discipline. He was a competent administrator and there was a marked development in cadetting and sports.

Rev. F. R. E. Mendis (principal 1931–1932)

Rev. F. R. E. Mendis (M.A. Cantab) served as the principal from 1931 to 1932. He started the library fund and developed cricket, soccer, boxing, and athletics.

H. Samaranayake (principal 1932–1933)

H. Samaranayake (B.A.) who was appointed as the principal in 1932 was the first Buddhist principal.

J. B. C. Rodrigo (principal 1933–1959)

J. B. C. Rodrigo (M.A. [Oxen] J.P.U.M.), was a very capable administrator and blessed with a great personality. The Teachers’ Guild, Cinema Association, Science Association, Drama Association, Red Cross branch, Sinhala and English Literary Associations, Debating Team, Co-operative Association, and hockey was initiated for the benefit of the students and new classrooms were built.^{[15][16][17][18][19]}

In 1933, the inaugural Battle of the Golds (Prince of Wales’ College vs. St. Sebastian's College) was held at the school grounds.

S. C. H. De Silva (principal 1959–1973)

S. C. H. De Silva (B.A., Dip. in School Admst) served the school for 14 years and there was a notable progression in the development of the school. Scouting was introduced and the Buddha shrine was constructed in 1967, ceremonially opened by Governor William Gopallawa. The Sinhala college anthem was written by B. Godahewa in 1967. Tissa Gunawardena joined the staff during this time. His works include the statues of the Buddha, the founding patron, and the largest Sandakadapahana in Sri Lanka.^[20] The Art Society and the Drama Club showed remarkable progress under his guidance. Gunawardena presented many stage plays, bringing out students' hidden talents.^[21]

L. H. Gunapala (principal 1973–1977)

L. H. Gunapala, who had served previously as a school inspector and as a district education inspector, was the principal during the school's centennial anniversary. The school was improved to a high standard and Hevisi and Western bands were formed during this time.

M. E. C. Fernando (principal 1977–1988)

M. E. C. Fernando, a former student and teacher succeeded Mr. Gunapala as principal.^[22] The H. R. Fernando Pavilion was gifted by former student Mr. H. R. Fernando. The cricket score board, library buildings, science and commerce buildings were some of these new additions. The sculpture of Sir Charles Henry de Soysa (sculpted by Mr. Tissa Gunawardena) was unveiled during this time. The venue of the annual Big Match was changed and was arranged to be held at De Soysa Stadium.

H. L. B. Gomes (principal 1989–1998)

H. L. B. Gomes (M.A.), who was an old boy, a teacher and vice-principal (during Mr M. E. C. Fernando's reign as principal), was appointed as principal in 1989. In his time, the school became one of the 15 National Schools in Sri Lanka. A new auditorium with the latest facilities and a computer department were introduced. Amongst other developments seen at the school during his tenure were making a qualitative improvement in education, expanding the school further by adding more facilities, namely: three, three-story buildings for Grade 11, the commerce section, and the primary grades; a new auditorium with the latest facilities; the canteens for students and teachers; initiating the construction of a new hostel; construction of the school office, principal's office, meeting hall and, toilets; the introduction of the Media Unit; and the construction of two playgrounds and cricket ground for the primary grades.

In 1998, the Western Band of the school had the rare privilege of welcoming the Prince of Wales, Prince Charles, who visited Sri Lanka in order to be part of its 50th Independence Day celebration. The school's cricket programme showed tremendous growth during this period, and this was reflected with Captain Suranga Wijenayake representing the National team.

Recent years

The 14th principal, D. A. Ramanayake, improved the computing department. S. J. P. Wijesinghe was the next principal and he was followed by K. Ratnaweera Perera and Rohana Karunaratne correspondingly. After tenures by W. Jayasena, Sampath Weragoda(Acting Principal) & J. W. S. Siriwardhana respectively. Kusala Fernando was the principal from 2017 to 2021. In 2014 the Hon. Jeewan Kumaranatunga allocated funding for the swimming pool project. The swimming pool was opened by the prime minister Hon.Ranil Wickremesinghe on 1 August 2017.

Battle of the Golds

Prince of Wales' College plays its annual Big Match with St. Sebastian's College, Moratuwa. It is also known as Battle of the Golds.^[26] Cricketers to have captained the school team include Wirantha Fernando and Kusal Mendis.^[27]