| 2001 | Martine Mitton | Ottawa Catholic School Board | Principal | $109,915 | $110,013 |
| 2002 | Anita Sabatini | Lambton Kent District School Board | Principal | $109,628 | $109,628 |
| 2003 | Rukshi Athulathmudali | Hamilton Wentworth Catholic District School Board | Principal | $109,562 | $110,201 |
| 2004 | Tera Brough | Hastings And Prince Edward District School Board | Principal | $109,531 | $109,531 |
| 2005 | Katrine Breton | Conseil Des Écoles Publiques De L’est De L’ontario | Direction école | $109,346 | $110,000 |
| 2006 | Mona Baléa | Conseil Scolaire Viamonde | Direction d’école | $109,293 | $109,939 |
| 2007 | Josée Dutrisac | Conseil Des Écoles Catholiques Du Centre Est | Direction d’école | $109,285 | $110,905 |
| 2008 | Krzysztof Rakuc | Lambton Kent District School Board | Principal | $109,202 | $109,202 |
| 2009 | Tania Gonsalves | Ottawa Catholic School Board | Principal | $108,722 | $108,820 |
| 2010 | Jennifer Ramsay | Ottawa-Carleton District School Board | Principal | $108,460 | $108,460 |
| 2011 | Hillary Howe | Superior-Greenstone District School Board | Principal | $108,388 | $108,388 |
| 2012 | Jocelyne Leclair | Conseil Scolaire De District Catholique Du Nouvel-Ontario | Direction d’école | $108,342 | $108,342 |
| 2013 | Amanda Gyori | Superior-Greenstone District School Board | Principal | $107,804 | $107,804 |
| 2014 | Valerie Dumoulin | District School Board Ontario North East | Principal | $107,623 | $107,721 |
| 2015 | Elizabeth Innes | District School Board Ontario North East | Principal | $107,306 | $107,405 |
| 2016 | Rhonda Garnier | Grand Erie District School Board | Principal | $107,130 | $107,130 |
| 2017 | Latha Reuben | Grand Erie District School Board | Principal | $107,130 | $107,130 |
| 2018 | Joanne Desantis | Algonquin And Lakeshore Catholic District School Board | School Principal | $107,030 | $107,030 |
| 2019 | David Dick | Algoma District School Board | Principal | $107,004 | $107,103 |
| 2020 | Mary Gingerich | Hamilton Wentworth Catholic District School Board | Principal | $106,991 | $107,630 |
| 2021 | Graham Purcell | Grand Erie District School Board | Principal | $106,919 | $106,919 |
| 2022 | Maureen Mchale-Enright | Renfrew County Catholic District School Board | Principal | $106,766 | $106,864 |
| 2023 | Jason Kennedy | Algoma District School Board | Principal | $106,684 | $106,783 |
| 2024 | Tara Constable | Algoma District School Board | Principal | $106,656 | $106,753 |
| 2025 | Jo Goossens | Waterloo Catholic District School Board | Principal | $106,458 | $106,458 |
| 2026 | Annette Gilbert | Thames Valley District School Board | Principal | $106,380 | $107,580 |
| 2027 | Shawn Darby | Thames Valley District School Board | Principal | $106,345 | $106,345 |
| 2028 | Amy Shamoon | Thames Valley District School Board | Principal | $106,239 | $106,239 |
| 2029 | Patricia Elcombe | Thames Valley District School Board | Principal | $106,239 | $106,239 |
| 2030 | Heinrich Bebie | Simcoe Muskoka Catholic District School Board | Principal | $106,160 | $106,160 |
| 2031 | Elisabeth Kaufmann | Thames Valley District School Board | Principal | $105,943 | $105,943 |
| 2032 | Arnold Potma | Education | Principal | $105,807 | $105,807 |
| 2033 | Kira Berry | Algoma District School Board | Principal | $105,565 | $105,664 |
| 2034 | Claude Mathieu | Conseil Des Écoles Publiques De L’est De L’ontario | Direction école | $105,474 | $106,127 |
| 2035 | Kurt Uriarte | Peel District School Board | Principal | $105,260 | $105,260 |
| 2036 | Carol Lucio | Algoma District School Board | Principal | $104,641 | $104,739 |
| 2037 | Sandi Tuzi | Dufferin-Peel Catholic District School Board | Principal | $104,211 | $105,116 |
| 2038 | Nicole Greco | Algoma District School Board | Principal | $103,895 | $103,994 |
| 2039 | Anita Treesh | Thunder Bay Catholic District School Board | Principal | $103,605 | $103,703 |
| 2040 | Ryan Gatto | Thunder Bay Catholic District School Board | Principal | $103,529 | $103,627 |
| 2041 | Paul Cook | Conseil Scolaire Viamonde | Direction d’école | $103,452 | $103,944 |
| 2042 | Stéphane Lewis | Conseil Scolaire Viamonde | Direction d’école | $103,039 | $103,531 |
| 2043 | Jennifer Tait | Thames Valley District School Board | Principal | $103,025 | $103,025 |
| 2044 | Tina Di Stefano | Conseil Scolaire Viamonde | Direction d’école | $103,019 | $103,511 |
| 2045 | Mary Beth Hurley | Near North District School Board | Principal | $102,843 | $102,843 |
| 2046 | Jessica Cameron | Conseil Scolaire Catholique Des Aurores Boréales | Direction d’école | $102,271 | $102,994 |
| 2047 | Ruth Mcnulty | Renfrew County Catholic District School Board | Principal | $101,955 | $102,053 |
| 2048 | Jeffrey Giovanatti | Algoma District School Board | Principal | $101,875 | $101,974 |
| 2049 | Lise Dewar | Conseil Scolaire De District Catholique Du Nouvel-Ontario | Direction d’école | $101,587 | $101,587 |
| 2050 | Annic Mongrain-Rush | Conseil Scolaire Catholique MonAvenir | Direction école | $100,915 | $101,465 |
| 2051 | Samuel Gélinas | Conseil Scolaire Viamonde | Direction d’école | $100,771 | $101,571 |