Founded in 1913
- 1913: Canadian Methodist Academy opens on September 13 with 13 students. Mrs. Ethel Gould Misener serves as principal until 1922.
- 1917: The Advisory Council, comprised of Christian mission groups whose seats were allocated according to the size of capital grants, is established. At this time, the word Methodist is dropped and the school becomes Canadian Academy.
- 1918: A high school is added to the main building. Inter-scholastic sports competition begins with a victorious baseball game over ASIJ.
- 1920: First graduation ceremony takes place at Kobe Union Church. The first edition of the school yearbook, known as the Red and Gold, contains 12 pages. First PTA Bazaar, predecessor of the Food Fair.
- 1921: Latin motto, Scientia Clavis Successus, created. School song written and composed. Canadian Senator Lorne Webster funds the new girl's dormitory, Webster Hall.
- 1922: Memorial Hall building dedicated in April, completed in October. The yearbook name, along with the school colors, is changed to Red and Grey due to the high price of gold ink. Mr. Graham Tench serves as second principal of CA.
- 1923: Memorial Hall opens. School houses refugees from the Tokyo earthquake.
- 1928: The purchase of property in Nagamine Heights, made possible by generous donations, begins a new era in CA history.
- 1929: The Duke of Gloucester dedicates a cairn at the site of Gloucester House dormitory on May 21. First field day held on new athletic ground.
- 1930: Mr. Kenneth Parker becomes principal.
- 1934: Boys move into new dormitory, Gloucester House. Rev. and Mrs. B.B. Chapman not only donate a substantial financial gift to fund the building project, they also become the house parents.
- 1940's: School seized by Japanese government for use as enemy alien property.
- 1942: Last formal graduation ceremony before the war. Instead of a professionally published Red and Grey, the books are mimeographed with photos stuck in place with photo corners.
- 1945: The extensive bombing of Kobe in February, March and June leaves three of CA's buildings (Memorial Hall, Webster Hall, and Misener Hall) in ruin. Only Gloucester House and the principal's residence at Nagamine survive.
- 1946: Occupation Forces use Gloucester House as a hostel.
- 1951: School property returned to previous owner and sponsor of the school, the United Church of Canada.
- 1952: School reopens on September 17 with 110 students. Arthur Menzies '34 presides at the opening in his role as the Canadian Embassy's Charge d'Affaires. Dr. Howard Norman '22 serves as principal.
- 1953: Cornerstone laid for new academic building. 40th anniversary edition of Red and Grey, first edition since the war, is published. Dr. Henry Warkentyne serves as acting principal.
- 1954: Mr. Alan Johns '39 serves as principal from '54-'58.
- 1958: Mr. Douglas Bishop serves as principal from '58-'64.
- 1963: Canadian Academy celebrates 50th anniversary.
- 1964: Mr. Gilbert Bascom serves as principal from '64-'71.
- 1966: The formal opening of Matsushita Gymnasium, which includes an auditorium, takes place on April 13.
- 1970: The first large scale Canadian Academy reunion takes place in Long Beach, California. The first issue of the Alumni Review is published.
- 1971: Under the guidance of Mrs. Unno, members of the Japanese culture club present their first kabuki performance. Mr. Albert Chudler serves as principal from '71-'74.
- 1972: CA accredited by the Western Association of Schools and Colleges (WASC).
- 1974: Mr. Donald Ballentine becomes headmaster.
- 1977: Dr. Guy Lott served as headmaster from '77-'81.
- 1981: A new elementary school and administration building was added to the Nagamine Heights campus. Mr. William Phend served as headmaster from '81-'83.
- 1982: Canadian Academy creates a middle school, housed in Misener House. New sports field named after Mr. Victor Mihara.
- 1983: Dr. Stuart Young served as headmaster from'83-'98.
- 1988: Canadian Academy celebrates its 75th anniversary and says 'Farewell' to Mr. Victor Mihara served the CA community as a teacher from 1952 to 1988. He influenced the school in many ways, including as a coach on the soccer field. He taught a surprisingly wide range of subjects over the years: from typing to Canadian history, from bookkeeping to shorthand.
- 1990: Under the leadership of Dr. Stuart Young and the Board of Trustees, the school and Gloucester House dormitory open on Rokko Island. On Transition Day, students and teachers walk all the way from the old school at Nagamine Heights to the new school on Rokko Island.
- 1992: Senior choir performs at New York's Lincoln Center.
- 1995: The Great Hanshin Earthquake devastates Kobe. Nearly 3,500 people seek shelter in school facilities.
- 1998: Dr. David Ottaviano becomes headmaster. Alumni gather for the Grand Reunion in Orlando, Florida. CA hosts its first Terry Fox Run to raise money for cancer research.
- 2000: Alumni gather in Kobe for the Millennium Reunion.
- 2003: Canadian Academy celebrates its 90th anniversary. Plans begun to build an activities center.
- 2005: Fred Wesson begins as headmaster.
- 2007: The Early Learning and Activities Center (ELAC) is completed in December 2007. Classes for BB, KA, and KB started in this addition to the CA campus in January 2008. The P&G Black Box Theater and a second gymnasium, new facilities in ELAC, provide additional flexibility and resources for Canadian Academy students and the CA community.
- 2008: Board of Trustees accepts new strategic plan, Morgan O'Hara '59 site-specific wall drawings were installed in ELAC, and an authentic Tea Ceremony room was constructed. Mr. and Mrs. Hamana from the International Division of Urasenke Foundation Headquarters in Kyoto honored CA by being the first guests of the new Tea Ceremony room.
- 2009: CA is re-accredited by WASC (Western Association of Schools and Colleges) and newly accredited by CIS (Council of International Schools).
- 2010: Artificial turf installed on large playing field.
- 2011: David Condon begins as Headmaster