| Solway Star v Helensburgh 01/12/1923 | View match | |
| Helensburgh v East Stirlingshire FC 08/12/1923 | View match | |
| Nithdale Wanderers v Helensburgh 15/12/1923 | View match | |
| Helensburgh v Clackmannan 22/12/1923 | View match | |
| Queen Of The South FC v Helensburgh 29/12/1923 | View match | |
| Helensburgh v Mid-Annandale 01/01/1924 | View match | |
| Arthurlie v Helensburgh 02/01/1924 | View match | |
| Galston v Helensburgh 05/01/1924 | View match | |
| Peebles Rovers v Helensburgh 19/01/1924 | View match | |
| Helensburgh v Solway Star 02/02/1924 | View match | |
| Helensburgh v Dumbarton Harp 09/02/1924 | View match | |
| Montrose FC v Helensburgh 16/02/1924 | View match |