| Pennant Hills AFL Club Footballer of the Year | Tim Scoular |
| Best Local First-Year Player (Ken Macrae Shield) | Connor Matthews |
| Club Person of the Year | Stewart Woodward |
| President’s Trophy | Sue & Nigel Blow |
| Senior Game Milestones | Sam Zikman (100+ games) |
| Sydney AFL Club Championship | Not awarded in 2021 |
Men’s Premier Division
| Men’s Premier Division Best & Fairest (Ern Holmes Trophy) | Luke Skrivanic |
| Men’s Premier Division Players’ Player Award | Wilson Mudge / Luke Skrivanic |
Men’s Premier Division Reserves
| Premier Division Reverses Best & Fairest (Angus McKernan Trophy) | Tim Scoular |
| Premier Division Reserves Players’ Player Award | Kieron Coaldrake |
Men’s Division 1
| Men’s Division 1 Best & Fairest | Kieran Wright |
| Men’s Division 1 Players’ Player Award | Anthony Woodward |
Men’s Division 2
| Men’s Division 2 Best & Fairest | Jake Woodward |
| Men’s Division 2 Players’ Player Award | Jake Woodward |
Men’s Division 3
| Men’s Division 3 Best & Fairest | Matthew Cassidy |
| Men’s Division 3 Players’ Player Award | Matthew Cassidy |
Men’s Masters
| Men’s Masters Best & Fairest | Kieran Wright |
| Men’s Masters Players’ Player Award | Kieran Wright |
Men’s U19’s Division 1
| Men’s U19’s Division 1 Best & Fairest (Lenny Hayes Trophy) | Christian Webster |
| Men’s U19’s Division 1 Players’ Player Award | Jonathan Moran |
Women’s Premier Division
| Women’s Premier Division Best & Fairest | Tayla Duguid |
| Women’s Premier Division Players Player | Tayla Duguid |
Women’s Division 1
| Women’s Premier Division 1 Best & Fairest | Caitlin Edmonds |
| Women’s Premier Division 1 Players Player | Amy Court |
Women’s Division 3
| Women’s Premier Division 3 Best & Fairest | Alyce Smith |
| Women’s Premier Division 3 Players Player | Alyce Smith |
Women’s Division 4
| Women’s Premier Division 4 Best & Fairest | Claudia Bilinski |
| Women’s Premier Division 4 Players Player | Claudia Bilinski |