| Saturday, 28/03/1959 | Penrith - Croatia | 0:3 | ||||||
| Monday, 30/03/1959 | Lansvale - Penrith | 1:0 | ||||||
| Saturday, 11/04/1959 | Penrith - Juventus | 1:2 | ||||||
| Saturday, 18/04/1959 | Five Dock - Penrith | 5:6 | ||||||
| Saturday, 25/04/1959 | Penrith - Fairfield Maltese | 0:0 | Award 3:0 | |||||
| Saturday, 02/05/1959 | Condell Park - Penrith | 4:2 | ||||||
| Saturday, 09/05/1959 | Penrith - Camperdown | 3:2 | ||||||
| Saturday, 23/05/1959 | Penrith - Toongabbie | 0:5 | ||||||
| Saturday, 30/05/1959 | University - Penrith | 4:3 | ||||||
| Saturday, 06/06/1959 | Penrith - Warriewood/Manly Warringah | 0:2 | ||||||
| Saturday, 13/06/1959 | Guildford - Penrith | 5:1 | ||||||
| Monday, 15/06/1959 | Nova - Penrith | 5:1 | ||||||
| Saturday, 20/06/1959 | Croatia - Penrith | 2:5 | ||||||
| Saturday, 27/06/1959 | Penrith - Lansvale | 3:7 | ||||||
| Saturday, 04/07/1959 | Penrith - Melita Eagles | 0:0 | Award 3:0 | |||||
| Saturday, 11/07/1959 | Juventus - Penrith | 1:4 | ||||||
| Saturday, 18/07/1959 | Penrith - Five Dock | 6:1 | ||||||
| Saturday, 25/07/1959 | Fairfield Maltese - Penrith | 10:4 | ||||||
| Saturday, 01/08/1959 | Penrith - Condell Park | 13:2 | ||||||
| Saturday, 08/08/1959 | Camperdown - Penrith | 3:2 | ||||||
| Saturday, 15/08/1959 | Penrith - Nova | 0:3 | ||||||
| Saturday, 22/08/1959 | Toongabbie - Penrith | 8:1 | ||||||
| Sunday, 23/08/1959 | Penrith - Guildford | 1:3 | ||||||
| Saturday, 29/08/1959 | Penrith - University | 2:8 | ||||||
| Saturday, 05/09/1959 | Warriewood/Manly Warringah - Penrith | 6:0 | ||||||
| Melita Eagles - Penrith | 2:2 |