School Year – Day School Programming
| School Year Begins | September 4, 2018 |
| Fall Term | September 4, 2018 – December 21, 2018 |
| Winter Term | January 7, 2019 -April 26, 2019 |
| Spring Term | April 29, 2019 – July 26, 2019 |
School Year – Extra-Curricular Programming
| Session A (10 Weeks) | September 4, 2019 – November 10, 2019 |
| Session B (10 Weeks) | November 12, 2019 – February 2, 2019 |
| Session C (10 Weeks) | February 4, 2019 – April 20, 2019 |
| Session D (10 Weeks) | April 22, 2019 – June 29, 2019 |
| Session E (8 Weeks) | July 1, 2019 – August 24, 2019 |
Holidays – Oak Learners Closed
| Labour Day | September 3, 2018 |
| Thanksgiving Day | October 8, 2018 |
| Winter Break (inclusive) | December 22, 2018 to January 6, 2019 |
| Family Day | February 18, 2019 |
| March Break (inclusive) | March 11 to March 16, 2018 |
| Good Friday | April 19, 2019 |
| Easter Monday | April 22, 2019 |
| Victoria Day Weekend | May 18, 19, 20, 2019 |
| Canada Day Weekend | June 29, June 30, July 1, 2019 |
| Civic Holiday | August 5, 2019 |
| End of Summer Closure | August 31, 2019 – September 2, 2019 |
Camp Dates
| PA Day Camps (TDSB,TCDSB) | October 6, November 17, December 1, January 19, February 16, June 8, June 21 |
| March Break Camp (2 weeks) | Week A – March 11 – March 15, 2019 (TDSB, TCDSB)
Week B – March 18 – March 22, 2019 |
| Summer Camps | July 2, 2019 – August 23, 2019 |
Special school events will be communicated via email, social media, and the school website.