| 1 | Fonda Loft | Halton District School Board | Department Head, Secondary | $155,830 | $155,830 |
| 2 | Randall Keast | Halton District School Board | Department Head, Secondary | $147,033 | $147,033 |
| 3 | Richard Jones | Waterloo Region District School Board | Department Head | $143,352 | $143,425 |
| 4 | Wendy Mendlow | Halton District School Board | Department Head, Secondary | $141,977 | $141,977 |
| 5 | Susan Dueckman | Halton District School Board | Department Head, Secondary | $138,342 | $138,342 |
| 6 | Peter Bird | Halton District School Board | Department Head, Secondary | $135,615 | $135,615 |
| 7 | Ryan Ibbott | Halton District School Board | Department Head, Secondary | $125,211 | $125,211 |
| 8 | Mark Kovich | Halton District School Board | Department Head, Secondary | $123,084 | $123,084 |
| 9 | Arnold Henkel | Waterloo Region District School Board | Department Head | $122,602 | $122,675 |
| 10 | Calvin Van Eek | Waterloo Region District School Board | Department Head | $118,773 | $118,846 |
| 11 | Reginald Holinshead | Waterloo Region District School Board | Department Head | $118,190 | $118,264 |
| 12 | Kyle Goodlet | Halton District School Board | Department Head, Secondary | $116,074 | $116,074 |
| 13 | Kyle Cowan | Windsor-Essex Catholic District School Board | Secondary Teacher - Department Head | $113,976 | $114,354 |
| 14 | James Young | Halton District School Board | Department Head, Secondary | $113,804 | $113,804 |
| 15 | Marc Messier | Halton District School Board | Department Head, Secondary | $113,598 | $113,598 |
| 16 | Sherry Freund | Waterloo Region District School Board | Department Head | $112,057 | $112,130 |
| 17 | Diane Nehmetallah | Windsor-Essex Catholic District School Board | Secondary Teacher - Department Head | $109,791 | $110,169 |
| 18 | Jolayne Conte | Windsor-Essex Catholic District School Board | Secondary Teacher - Department Head | $109,485 | $109,863 |
| 19 | Lindsay Cheal | Halton Catholic District School Board | Secondary Department Head | $108,615 | $108,694 |
| 20 | Liana Cote-Montminy | Windsor-Essex Catholic District School Board | Secondary Teacher - Department Head | $108,240 | $108,618 |
| 21 | Melissa Giardina | Halton Catholic District School Board | Secondary Department Head | $108,131 | $108,210 |
| 22 | John Kosir | Halton Catholic District School Board | Secondary Department Head | $108,075 | $108,154 |
| 23 | Valerie Kelenc | Halton Catholic District School Board | Secondary Department Head | $107,851 | $107,930 |
| 24 | Stacey McClounie | Windsor-Essex Catholic District School Board | Secondary Teacher - Department Head | $107,575 | $107,953 |
| 25 | Amy Westenberg | Halton District School Board | Department Head, Secondary | $107,561 | $107,561 |