School Year – Day School Programming
| School Year Begins | September 3, 2019 |
| Fall Term | September 3, 2019 – December 20, 2019 |
| Winter Term | January 6, 2020 -April 24, 2020 |
| Spring Term | April 27, 2020 – July 31, 2020 |
School Year – Extra-Curricular Programming
| Fall | September 3, 2019 – December 20, 2019 |
| Winter | January 6, 2020 – April 24, 2020 |
| Spring | April 27, 2020 – July 31, 2020 |
Holidays – Oak Learners Closed
| Labour Day | September 2, 2019 |
| Thanksgiving Day | October 14, 2019 |
| Winter Break (inclusive) | December 21, 2019 to January 5, 2020 |
| Family Day | February 17, 2020 |
| March Break (inclusive) | March 16 to March 20, 2020 |
| Good Friday | April 10, 2020 |
| Easter Monday | April 13, 2020 |
| Victoria Day Weekend | May 18 2020 |
| Canada Day Break | June 27 to July 5, 2020 |
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.