USA: Dallas - Singles - Main |
| 1/16-finals | McClune M. | Jenkins S. | 2:0 (6:3, 6:3) | details | 01.02.2010 |
USA: Champaign - Singles - Main |
| | Jenkins S. | Sweeting R. | 0:2 (3:6, 2:6) | details | 17.11.2009 |
USA: Knoxville - Singles - Main |
| | Dent T. | Jenkins S. | 2:1 (6:7, 6:4, 6:2) | details | 11.11.2009 |
USA: Charlottesville - Singles - Main |
| | Singh S. | Jenkins S. | 2:1 (1:6, 7:6, 6:4) | details | 05.11.2009 |
| | Jenkins S. | Parr C. | 2:1 (6:1, 5:7, 6:3) | details | 03.11.2009 |
USA: Sacramento - Singles - Main |
| | Jenkins S. | Levine J. | 0:2 (1:6, 1:6) | details | 09.10.2009 |
| | Jenkins S. | Sorensen L. | 2:1 (6:3, 5:7, 6:3) | details | 08.10.2009 |
| | Karanusic R. | Jenkins S. | 0:2 (6:7, 2:6) | details | 06.10.2009 |
USA: Tulsa - Singles - Main |
| | Jenkins S. | Levine J. | 0:2 (1:6, 1:6) | details | 17.09.2009 |
| | Jenkins S. | Cook L. | 2:0 (6:3, 6:2) | details | 14.09.2009 |
USA: US Open - Singles - Qualification |
| Final | Bellucci T. | Jenkins S. | 2:0 (6:2, 6:4) | details | 28.08.2009 |
| Semi-finals | McClune M. | Jenkins S. | 0:2 (3:6, 4:6) | details | 27.08.2009 |
| Quarter-finals | Jenkins S. | Hrbaty D. | 2:0 (6:3, 6:4) | details | 25.08.2009 |
Canada: Vancouver - Singles - Main |
| 1/8-finals | Jenkins S. | Bogdanovic A. | 1:2 (6:3, 614:7, 4:6) | details | 06.08.2009 |
| 1/16-finals | Ram R. | Jenkins S. | 0:2 (64:7, 4:6) | details | 04.08.2009 |
USA: Lexington - Singles - Main |
| 1/16-finals | Jenkins S. | Cook L. | 0:1 RET. (4:6, 0:1) | details | 21.07.2009 |
USA: Aptos - Singles - Main |
| 1/16-finals | Jenkins S. | Kuznetsov Al. | 1:2 (4:6, 6:1, 61:7) | details | 14.07.2009 |
USA: Winnetka - Singles - Main |
| Quarter-finals | De Heart R. | Jenkins S. | 2:0 (7:64, 6:2) | details | 03.07.2009 |
| 1/8-finals | Okun N. | Jenkins S. | 1:2 (6:2, 3:6, 4:6) | details | 02.07.2009 |
| 1/16-finals | Jenkins S. | Stoppini A. | 2:1 (7:65, 3:6, 7:63) | details | 30.06.2009 |
United Kingdom: Wimbledon - Singles - Qualification |
| Quarter-finals | Jenkins S. | Roger-Vasselin E. | 1:2 (7:6, 3:6, 0:6) | details | 15.06.2009 |
United Kingdom: Nottingham - Singles - Main |
| 1/16-finals | Jenkins S. | Goodall J. | 1:2 (7:64, 4:6, 63:7) | details | 02.06.2009 |
Italy: Alessandria - Singles - Main |
| 1/8-finals | Jenkins S. | Levine J. | 1:2 (6:1, 64:7, 2:6) | details | 27.05.2009 |
| 1/16-finals | Haider-Maurer A. | Jenkins S. | 1:2 (3:6, 6:2, 63:7) | details | 25.05.2009 |
France: French Open - Singles - Qualification |
| Semi-finals | Jenkins S. | Brands D. | 1:2 (5:7, 6:1, 3:6) | details | 21.05.2009 |
| Quarter-finals | Bubka S. | Jenkins S. | 1:2 (6:7, 6:4, 4:6) | details | 19.05.2009 |
USA: Sarasota - Singles - Main |
| 1/8-finals | Jenkins S. | Dasnieres de Veigy J. | 0:1 RET. (4:6, 1:2) | details | 13.05.2009 |
| 1/16-finals | Jenkins S. | Todero N. | 2:0 (6:2, 7:63) | details | 11.05.2009 |
USA: Savannah - Singles - Main |
| 1/16-finals | Jenkins S. | Witten J. | 0:0 RET. (0:2) | details | 05.05.2009 |
USA: Tallahassee - Singles - Main |
| 1/16-finals | Jenkins S. | Isner J. | 0:2 (4:6, 1:6) | details | 22.04.2009 |
USA: Houston - Singles - Main |
| 1/8-finals | Jenkins S. | Phau B. | 0:2 (4:6, 6:7) | details | 09.04.2009 |
| 1/16-finals | Peya A. | Jenkins S. | 1:2 (6:0, 4:6, 3:6) | details | 07.04.2009 |
USA: Baton Rouge - Singles - Main |
| 1/16-finals | Obradovic V. | Jenkins S. | 2:0 (6:4, 6:4) | details | 07.04.2009 |
USA: Indian Wells - Singles - Qualification |
| | Kim K. | Jenkins S. | 2:1 (6:7, 6:2, 6:1) | details | 11.03.2009 |
| | Jenkins S. | Warburg S. | 2:0 (6:2, 6:3) | details | 10.03.2009 |
France: Cherbourg - Singles - Main |
| 1/8-finals | Jenkins S. | Mannarino A. | 0:2 (2:6, 4:6) | details | 05.03.2009 |
| 1/16-finals | Jenkins S. | Faurel J. | 2:0 (6:3, 6:1) | details | 03.03.2009 |
Germany: Wolfsburg - Singles - Main |
| 1/16-finals | Bachinger M. | Jenkins S. | 2:1 (67:7, 6:4, 6:2) | details | 24.02.2009 |
Serbia: Belgrade - Singles - Main |
| 1/16-finals | Jenkins S. | Stakhovsky S. | 0:2 (3:6, 4:6) | details | 18.02.2009 |
USA: Dallas - Singles - Main |
| Quarter-finals | Amritraj P. | Jenkins S. | 2:1 (7:63, 4:6, 6:4) | details | 05.02.2009 |
| 1/8-finals | Jenkins S. | Levine J. | 2:0 (6:4, 6:1) | details | 05.02.2009 |
| 1/16-finals | Jenkins S. | Faurel J. | 2:1 (6:3, 3:6, 6:4) | details | 04.02.2009 |
USA: Carson - Singles - Main |
| Final | Odesnik W. | Jenkins S. | 2:0 (6:4, 6:4) | details | 01.02.2009 |
| Semi-finals | Jenkins S. | Kim K. | 2:0 (6:4, 6:3) | details | 31.01.2009 |
| Quarter-finals | Jenkins S. | Mamiit C. | 2:0 (6:3, 6:4) | details | 30.01.2009 |
| 1/8-finals | Jenkins S. | Lapentti G. | 2:1 (67:7, 7:5, 7:61) | details | 29.01.2009 |
| 1/16-finals | Devvarman S. | Jenkins S. | 0:2 (1:6, 4:6) | details | 27.01.2009 |
Australia: Australian Open - Singles - Qualification |
| 1/64-finals | Chiudinelli M. | Jenkins S. | 2:0 (6:3, 6:1) | details | 14.01.2009 |