| San Diego | Round | Result | H | A | 
		
			| 12.10. |  | Gauff C. - Montgomery R. | 1R | 6-3, 6-3 | 1.15 | 5.51 | 
		
			| 09.10. |  | Montgomery R. - Pera B. | Q-R16 | 1-6, 6-1, 6-4 | 3.23 | 1.32 | 
		
			| 09.10. |  | Montgomery R. - Zhang S. | Q-1R | 6-2, 6-3 | 3.77 | 1.25 | 
		
			| Rancho Santa Fe 2 ITF | Round | Result | H | A | 
		
			| 06.10. |  | Kalieva E. - Montgomery R. | R16 | 6-2, 2-6, 7-61 | 2.71 | 1.41 | 
		
			| 05.10. |  | Montgomery R. - Harrison C. | 1R | 6-4, 7-63 | 1.62 | 2.13 | 
		
			| Templeton ITF | Round | Result | H | A | 
		
			| 02.10. |  | Brengle M. - Montgomery R. | F | 4-6, 6-4, 6-2 | 1.37 | 2.84 | 
		
			| 01.10. |  | Montgomery R. - Volodko K. | SF | 6-3, 6-1 | 1.51 | 2.41 | 
		
			| 01.10. |  | Montgomery R. - Kawa K. | QF | 6-3, 6-1 | 1.90 | 1.81 | 
		
			| 29.09. |  | Montgomery R. - Duval V. | R16 | 6-1, 6-2 | 1.44 | 2.59 | 
		
			| 29.09. |  | Montgomery R. - Sakatsume H. | 1R | 6-2, 3-6, 6-2 | 1.44 | 2.59 | 
		
			| 27.09. |  | Montgomery R. - Osborne A. | Q-R16 | 7-5, 6-1 | 1.06 | 6.77 | 
		
			| 26.09. |  | Montgomery R. - Bunch K. | Q-1R | 6-2, 6-1 | 1.05 | 7.94 | 
		
			| Berkeley ITF | Round | Result | H | A | 
		
			| 22.09. |  | Chirico L. - Montgomery R. | R16 | 3-6, 6-2, 6-4 | 1.62 | 2.17 | 
		
			| 21.09. |  | Montgomery R. - Gailis R. | 1R | 6-4, 6-3 | 1.19 | 4.18 | 
		
			| 20.09. |  | Montgomery R. - Osborne A. | Q-R16 | 6-2, 6-1 | 1.10 | 5.73 | 
		
			| 19.09. |  | Montgomery R. - Newborn R. | Q-1R | 6-3, 6-3 | 1.06 | 6.89 | 
		
			| Nottingham 9 ITF | Round | Result | H | A | 
		
			| 13.05. |  | Silva E. - Montgomery R. | QF | 6-3, 6-4 | 2.45 | 1.48 | 
		
			| 12.05. |  | Montgomery R. - Ozgen P. | R16 | 6-4, 6-2 | 1.35 | 2.92 | 
		
			| 10.05. |  | Montgomery R. - Wu H. | 1R | 6-4, 6-4 | 1.09 | 6.14 | 
		
			| Nottingham 8 ITF | Round | Result | H | A | 
		
			| 03.05. |  | Stollar F. - Montgomery R. | 1R | 7-5, 7-5 | 2.69 | 1.40 | 
		
			| Nottingham 7 ITF | Round | Result | H | A | 
		
			| 24.04. |  | Silva E. - Montgomery R. | F | 6-4, 6-4 | 3.40 | 1.27 | 
		
			| 23.04. |  | Montgomery R. - Sebov K. | SF | 4-1 | 1.68 | 2.06 | 
		
			| 22.04. |  | Montgomery R. - Garland J. | QF | 6-3, 6-3 | 1.52 | 2.36 | 
		
			| 21.04. |  | Montgomery R. - Radwanska U. | R16 | 7-66, 6-2 | 1.69 | 2.01 | 
		
			| 19.04. |  | Montgomery R. - Lukosiute A. | 1R | 1-6, 7-64, 7-5 | 1.12 | 4.81 | 
		
			| Miami | Round | Result | H | A | 
		
			| 23.03. |  | Kalinskaya A. - Montgomery R. | 1R | 4-6, 6-4, 7-64 | 1.15 | 5.44 | 
		
			| Indian Wells | Round | Result | H | A | 
		
			| 09.03. |  | Kanepi K. - Montgomery R. | 1R | 6-3, 6-3 | 1.20 | 4.54 | 
		
			| Arcadia ITF | Round | Result | H | A | 
		
			| 03.03. |  | Marino R. - Montgomery R. | R16 | 6-4, 6-3 | 1.42 | 2.65 | 
		
			| 02.03. |  | Montgomery R. - Loeb J. | 1R | 7-63, 7-67 | 1.49 | 2.42 | 
		
			| 01.03. |  | Montgomery R. - Wolff V. | Q-R16 | 6-2, 7-64 | 1.09 | 6.46 | 
		
			| 28.02. |  | Montgomery R. - Pursoo A. | Q-1R | 6-1, 6-4 | 1.16 | 4.38 | 
		
			| Orlando 4 ITF | Round | Result | H | A | 
		
			| 27.01. |  | Wang X. - Montgomery R. | 1R | 3-6, 6-3, 6-2 | 1.43 | 2.63 | 
		
			| 25.01. |  | Montgomery R. - Kiick A. | Q-R16 | 6-2, 7-5 | 1.56 | 2.24 | 
		
			| 24.01. |  | Montgomery R. - Proctor L. | Q-1R | 6-3, 6-3 | 1.24 | 3.59 |