| Sorrento 2 ITF | Round | Result | H | A | 
		
			| 02.12. |  | Windley J. - Calderwood T. | 1R | 6-2, 6-1 |  |  | 
		
			| 01.12. |  | Calderwood T. - Antonic M. | Q-R16 | 4-6, 6-4, 6-1 |  |  | 
		
			| 30.11. |  | Calderwood T. - Tepper B. | Q-2R | 6-3, 6-0 |  |  | 
		
			| Perth ITF | Round | Result | H | A | 
		
			| 23.11. |  | Cuthbertson J. - Calderwood T. | Q-2R | 6-4, 7-61 |  |  | 
		
			| Port Pirie ITF | Round | Result | H | A | 
		
			| 21.10. |  | Prousis A. - Calderwood T. | 1R | 6-3, 6-2 |  |  | 
		
			| 20.10. |  | Calderwood T. - Le J. | Q-R16 | 6-3, 6-2 |  |  | 
		
			| 19.10. |  | Calderwood T. - Daw L. | Q-2R | 3-6, 6-2, 6-1 |  |  | 
		
			| Mount Gambier ITF | Round | Result | H | A | 
		
			| 12.10. |  | Moriarty J. - Calderwood T. | Q-2R | 7-5, 2-6, 6-2 |  |  | 
		
			| Traralgon ITF | Round | Result | H | A | 
		
			| 06.10. |  | Rogowska O. - Calderwood T. | Q-R16 | 6-3, 6-1 |  |  | 
		
			| 05.10. |  | Calderwood T. - Ruxton K. | Q-2R | 4-6, 6-3, 6-4 |  |  | 
		
			| Kawana ITF | Round | Result | H | A | 
		
			| 17.09. |  | Hubacek A. - Calderwood T. | R16 | 3-6, 6-3, 7-64 |  |  | 
		
			| 16.09. |  | Calderwood T. - Du Plessis L. | 1R | 7-64, 6-1 |  |  | 
		
			| Rockhampton ITF | Round | Result | H | A | 
		
			| 09.09. |  | Zhou Y. - Calderwood T. | 1R | 6-3, 6-4 |  |  | 
		
			| London - Cumberland ITF | Round | Result | H | A | 
		
			| 14.08. |  | Babakova M. - Calderwood T. | QF | 6-2, 6-4 |  |  | 
		
			| 13.08. |  | Calderwood T. - Sargeant A. | R16 | 6-3, 6-0 |  |  | 
		
			| 12.08. |  | Calderwood T. - De Lattre M. | 1R |  |  |  | 
		
			| Coimbra ITF | Round | Result | H | A | 
		
			| 02.08. |  | Barritza K. - Calderwood T. | Q-1R | 7-5, 6-0 |  |  | 
		
			| Vigo ITF | Round | Result | H | A | 
		
			| 27.07. |  | Sainz-Pelegri L. - Calderwood T. | Q-2R | 6-4, 6-3 |  |  | 
		
			| Sorrento ITF | Round | Result | H | A | 
		
			| 18.03. |  | Sheed B. - Calderwood T. | 1R | 7-62, 6-3 |  |  | 
		
			| 17.03. |  | Calderwood T. - Scivetti D. | Q-R16 | 6-3, 6-4 |  |  | 
		
			| 16.03. |  | Calderwood T. - Ericksen H. | Q-2R | 6-3, 6-4 |  |  | 
		
			| Kalgoorlie ITF | Round | Result | H | A | 
		
			| 12.03. |  | Bai A. - Calderwood T. | R16 | 6-4, 6-2 |  |  | 
		
			| 11.03. |  | Calderwood T. - Patterson T. | 1R | 7-5, 4-6, 6-3 |  |  |