The original St. John Bosco School was built in 1944 by the Humberstone Village Separate School Board. It consisted of 3 rooms, Grade 1 & 2, Grade 3, 4, 5, Grade 6, 7, and 8. Three more rooms were added in 1953 - 54.

Holy Cross School was built in 1967. A new addition consisting of five rooms, a Library, and change rooms was added to Holy Cross in 1999 to form the New St. John Bosco School on Highland Avenue. The Official Blessing was held on October 4th, 1999 to re-name the new site St. John Bosco School. The principal of the amalgamated schools was John Boyer. The Holy Cross Library was dedicated in March 2004 with a commemorative plaque.

Total enrolment as of September 2011: 282