| w 18 | Sat 8/5 | SOS Hills District - North Rocks |  Bold Horizons Event Organiser | Orienteering NSW | 61 | FP | loc | | M | | |  |
| SOS Newcastle - Broadmeadow | Bold Horizons Event Organiser | Orienteering NSW | 48 | | club | | S | | | |
| SOS Northside - Pennant Hills | Bold Horizons Event Organiser | Orienteering NSW | 59 | | loc | | M | | | |
| BH Navigation Skills Training | Bold Horizons Event Organiser | Orienteering NSW | - | | loc | | M | | | |
| IKO local - Figtree |  Illawarra Kareelah Orienteers | Orienteering NSW | 25 | | loc | | M | | | |
| Sun 9/5 | Central Coast Winter Park-O #1 - Hylton Moore Park, East Gosford |  Central Coast Orienteers | Orienteering NSW | 5 | FP | loc | | M | | | |
| Newcastle Pairs - Minmi |  Newcastle Orienteering Club | Orienteering NSW | 38 | | loc | | M | | | |
| Coffs Winter #1 |  Bush n Beach Orienteering Club | Orienteering NSW | 27 | | club | | L | | | |
| Waggaroos Local Bush |  Wagga and Riverina Occasional Orienteers | Orienteering NSW | 10 | | loc | | M | | | |
| w 19 | Mon 10/5 | | | | | | | | | | | |
| Tue 11/5 | O Training | Bold Horizons Event Organiser | Orienteering NSW | 0 | | club | | M | | | |
| Wed 12/5 | | | | | | | | | | | |
| Thu 13/5 | | | | | | | | | | | |
| Fri 14/5 | | | | | | | | | | | |
| Sat 15/5 | 2021 Wildfire Sports Autumn Classics Prelude Sprint |  Orienteering ACT
 Orienteering NSW
 Red Roos | Orienteering ACT
Orienteering NSW | 193 | | sta | | S | | | |
| NOL, ACT League #4, NSW SL #3: Broulee Dunes | Orienteering ACT
Orienteering NSW
Red Roos | Orienteering ACT
Orienteering NSW | 432 | | nat | | M | | | |
| Sun 16/5 | NOL, ACT League #5, NSW SL #4: Broulee Dunes | Orienteering ACT
Orienteering NSW
Red Roos | Orienteering ACT
Orienteering NSW | 331 | | nat | | M | | | |
| HOG Laurieton Orienteering May 2021 |  Hastings Orienteering Group | Orienteering NSW | 60 | FP | loc | | M | | | |
| w 20 | Mon 17/5 | | | | | | | | | | | |
| Tue 18/5 | O Training | Bold Horizons Event Organiser | Orienteering NSW | 0 | | club | | L | | | |
| Wed 19/5 | Moonlight Madness 2 - Woolwich |  Garingal Orienteers | Orienteering NSW | 83 | FP | loc | | M | N | | |
| Thu 20/5 | | | | | | | | | | | |
| Fri 21/5 | | | | | | | | | | | |
| Sat 22/5 | SOS Hills District 3 Term 2 - Castle Hill | Bold Horizons Event Organiser | Orienteering NSW | 73 | FP | loc | | M | | | |
| SOS Newcastle 3 - Waratah | Bold Horizons Event Organiser | Orienteering NSW | 34 | | club | | S | | | |
| SOS Northside 3 Term 2 - combined with Hills District | Bold Horizons Event Organiser | Orienteering NSW | - | FP | loc | | M | | | |
| Sun 23/5 | Sydney Metro League #3 |  Bennelong Northside Orienteers | Orienteering NSW | 189 | FP | loc | | M | | |  |
| Armidale Pine Forest |  Northern Tablelands Orienteering Club | Orienteering NSW | 30 | | loc | | L | | | |
| w 21 | Mon 24/5 | | | | | | | | | | | |
| Tue 25/5 | Training - Twin Creeks Turramurra | Bold Horizons Event Organiser | Orienteering NSW | 4 | | club | | L | | | |
| Wed 26/5 | | | | | | | | | | | |
| Thu 27/5 | | | | | | | | | | | |
| Fri 28/5 | | | | | | | | | | | |
| Sat 29/5 | SOS Northside - West Pymble Results | Bold Horizons Event Organiser | Orienteering NSW | 118 | | club | | L | | | |
| SOS - Hills District - The Ponds | Bold Horizons Event Organiser | Orienteering NSW | 89 | FP | loc | | S | | | |
| SOS Newcastle - Broadmeadow | Bold Horizons Event Organiser | Orienteering NSW | 0 | | club | | L | | | |
| SOS Newcastle - Broadmeadow results | Bold Horizons Event Organiser | Orienteering NSW | 57 | | club | | S | | | |
| SOS Northside - West Pymble | Bold Horizons Event Organiser | Orienteering NSW | 0 | FP | loc | | M | | | |
| Sun 30/5 | 2021 NOY 3 - Pelton/Bellbird | Newcastle Orienteering Club | Orienteering NSW | 97 | | loc | | M | | | |
| Waggaroos Local Sprint | Wagga and Riverina Occasional Orienteers | Orienteering NSW | 17 | FP | loc | | S | | | |
| Highlands Forest Series #2 - Penrose |  Southern Highlands Orienteers | Orienteering NSW | 44 | | club | | M | | | |
| w 22 | Mon 31/5 | | | | | | | | | | | |
| Tue 1/6 | Training - Twin Creeks, Turramurra | Bold Horizons Event Organiser | Orienteering NSW | 2 | | club | | L | | | |
| Wed 2/6 | | | | | | | | | | | |
| Thu 3/6 | | | | | | | | | | | |
| Fri 4/6 | | | | | | | | | | | |
| Sat 5/6 | SOS Hills District - Baulkham Hills | Bold Horizons Event Organiser | Orienteering NSW | 54 | FP | loc | | S | | | |
| SOS Newcastle | Bold Horizons Event Organiser | Orienteering NSW | 0 | | club | | S | | | |
| SOS Northside - Lindfield | Bold Horizons Event Organiser | Orienteering NSW | 57 | FP | loc | | M | | | |
| IKO Local - Sutherland | Illawarra Kareelah Orienteers | Orienteering NSW | 28 | | loc | | M | | | |
| Sun 6/6 | The Great Nosh Footrace Trail Run | Bennelong Northside Orienteers
Bold Horizons Event Organiser | Orienteering NSW | - | | loc | | L | | | |
| Central Coast Winter Park-O #2 - Mount Penang | Central Coast Orienteers | Orienteering NSW | 19 | FP | loc | | M | | | |
| Bush Series #3 Rocky Falls |  Goldseekers Orienteers | Orienteering NSW | 29 | | club | | L | | | |
| Coffs Winter #2 | Bush n Beach Orienteering Club | Orienteering NSW | 24 | FP | club | | L | | | |
| w 23 | Mon 7/6 | | | | | | | | | | | |
| Tue 8/6 | Training | Bold Horizons Event Organiser | Orienteering NSW | - | | club | | L | | | |
| Wed 9/6 | | | | | | | | | | | |
| Thu 10/6 | | | | | | | | | | | |
| Fri 11/6 | | | | | | | | | | | |
| Sat 12/6 | 2021 Queens Birthday 3 Days / NSW State League 5 to 7 - Multi Day Entry , sL5 - Middle Distance - Freemans Waterhole | Newcastle Orienteering Club | Orienteering NSW | 329 | | sta | | M | | | |
| Sun 13/6 | 2021 Queens Birthday 3 Days / NSW State League 5 to 7 - Multi Day Entry , sL6 - Long Distance - Quorrobolong | Newcastle Orienteering Club | Orienteering NSW | 334 | | sta | | L | | | |
| w 24 | Mon 14/6 | 2021 Queens Birthday 3 Days / NSW State League 5 to 7 - Multi Day Entry , sL7 - Sprint - Cooranbong | Newcastle Orienteering Club | Orienteering NSW | 325 | | sta | | S | | | |
