| Futures 08 | Round | Result | H | A | 
		
			| 25.11. |  | Molchanov D. - Grozdanov T. | 1R | 3-6, 7-5, 6-3 |  |  | 
		
			| 18.11. |  | Molchanov D. - Grozdanov T. | 1R | 4-6, 6-4, 7-5 |  |  | 
		
			| Bucharest challenger | Round | Result | H | A | 
		
			| 18.09. |  | Enev T. - Grozdanov T. | Q-1R | 6-3, 7-5 |  |  | 
		
			| Futures 08 | Round | Result | H | A | 
		
			| 13.09. |  | Grozdanov T. - Traykov I. | F | 7-5, 1-0 |  |  | 
		
			| 12.09. |  | Grozdanov T. - Grabul D. | SF | 6-4, 6-3 |  |  | 
		
			| 11.09. |  | Grozdanov T. - Puscasu P. | QF | 5-7, 6-4, 6-0 |  |  | 
		
			| 10.09. |  | Grozdanov T. - Lazov A. | R16 | 6-1, 6-4 |  |  | 
		
			| 09.09. |  | Grozdanov T. - Alcorta-Olarra G. | 1R | 4-6, 6-4, 6-2 |  |  | 
		
			| 04.09. |  | Enev T. - Grozdanov T. | QF | 6-4, 6-2 |  |  | 
		
			| 03.09. |  | Grozdanov T. - Cvetkov A. | R16 | 6-0, 6-1 |  |  | 
		
			| 02.09. |  | Grozdanov T. - Mihov T. | 1R | 6-3, 6-2 |  |  | 
		
			| 27.08. |  | Alekseenko V. - Grozdanov T. | R16 | 4-6, 6-2, 7-5 |  |  | 
		
			| 26.08. |  | Grozdanov T. - Dimov V. | 1R | 6-1, 6-3 |  |  | 
		
			| 21.08. |  | Mladenov V. - Grozdanov T. | QF | 6-4, 2-6, 6-4 |  |  | 
		
			| 20.08. |  | Grozdanov T. - Lazov A. | R16 | 6-4, 6-4 |  |  | 
		
			| 19.08. |  | Grozdanov T. - Dimov V. | 1R | 6-3, 6-3 |  |  | 
		
			| Istanbul 3 challenger | Round | Result | H | A | 
		
			| 09.08. |  | Kohlmann M. - Grozdanov T. | Q-R16 | 7-6, 2-6, 6-4 |  |  | 
		
			| Futures 08 | Round | Result | H | A | 
		
			| 10.07. |  | Canudas-Fernandez D. - Grozdanov T. | QF | 6-1, 6-0 |  |  | 
		
			| 09.07. |  | Grozdanov T. - Vardhan V. | R16 | 7-62, 7-5 |  |  | 
		
			| 08.07. |  | Grozdanov T. - Popovic P. | 1R | 3-6, 6-2, 7-5 |  |  | 
		
			| 01.07. |  | Erguden B. - Grozdanov T. | 1R | 6-4, 6-4 |  |  | 
		
			| Constanta challenger | Round | Result | H | A | 
		
			| 21.06. |  | Enev T. - Grozdanov T. | Q-1R | 7-5, 6-3 |  |  | 
		
			| Futures 08 | Round | Result | H | A | 
		
			| 17.06. |  | Maamoun K. - Grozdanov T. | 1R | 6-2, 6-2 |  |  | 
		
			| Sofia challenger | Round | Result | H | A | 
		
			| 10.06. |  | Sidorenko A. - Grozdanov T. | 1R | 6-2, 6-7, 6-2 | 1.25 | 3.00 | 
		
			| Futures 08 | Round | Result | H | A | 
		
			| 31.05. |  | Mertens Y. - Grozdanov T. | F | 6-1, 6-3 |  |  | 
		
			| 30.05. |  | Grozdanov T. - Viola M. | SF | 6-4, 6-4 |  |  | 
		
			| 29.05. |  | Grozdanov T. - Leonte B. | QF | 6-3, 6-4 |  |  | 
		
			| 28.05. |  | Grozdanov T. - Simoni M. | R16 | 3-6, 6-3, 6-4 |  |  | 
		
			| 27.05. |  | Grozdanov T. - Kamynin D. | 1R | 7-5, 6-4 |  |  | 
		
			| 22.05. |  | Pujo X. - Grozdanov T. | QF | 7-5, 6-0 |  |  | 
		
			| 21.05. |  | Grozdanov T. - Sabate-Bretos O. | R16 | 6-2, 6-2 |  |  | 
		
			| 20.05. |  | Grozdanov T. - Mlendea A. | 1R | 6-1, 7-5 |  |  | 
		
			| 15.05. |  | Traykov I. - Grozdanov T. | QF | 6-1, 6-4 |  |  | 
		
			| 14.05. |  | Grozdanov T. - Kanev Y. | R16 | 6-2, 6-1 |  |  | 
		
			| 13.05. |  | Grozdanov T. - Fattar A. | 1R | 6-1, 63-7, 6-4 |  |  | 
		
			| 07.05. |  | Traykov I. - Grozdanov T. | R16 | 6-3, 6-4 |  |  | 
		
			| 06.05. |  | Grozdanov T. - Dimov V. | 1R | 6-1, 6-4 |  |  | 
		
			| 23.03. |  | Fattar A. - Grozdanov T. | Q-3R | 7-5, 6-4 |  |  | 
		
			| 22.03. |  | Grozdanov T. - Gotman S. | Q-2R | 6-1, 6-2 |  |  | 
		
			| 21.03. |  | Grozdanov T. - Karaliolios E. | Q-1R | 6-4, 6-4 |  |  | 
		
			| 20.03. |  | Vejmelka A. - Grozdanov T. | QF | 6-4, 6-1 |  |  | 
		
			| 19.03. |  | Grozdanov T. - Sousa P. | R16 | 6-0, 6-3 |  |  | 
		
			| 18.03. |  | Grozdanov T. - Altuna T. | 1R | 6-1, 6-2 |  |  | 
		
			| 17.03. |  | Grozdanov T. - Kushev I. | Q-R16 | 3-1 |  |  | 
		
			| 16.03. |  | Grozdanov T. - Khachatryan A. | Q-3R | 6-1, 6-1 |  |  | 
		
			| 15.03. |  | Grozdanov T. - Ozmeral A. | Q-2R | 6-1, 6-1 |  |  | 
		
			| 16.02. |  | Sancic A. - Grozdanov T. | Q-1R | 6-2, 6-2 |  |  | 
		
			| 11.02. |  | Poljancic B. - Grozdanov T. | Q-R16 | 4-6, 6-2, 7-65 |  |  | 
		
			| 10.02. |  | Grozdanov T. - Schalomov P. | Q-2R | 6-3, 5-7, 7-67 |  |  | 
		
			| 09.02. |  | Grozdanov T. - Raguz R. | Q-1R | 6-3, 7-64 |  |  |