 USA: Savannah - Singles - Main |
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| 1/16-finals | Janvier M. | Kypson P. | 2:1 (3:6, 7:65, 6:4) | details | 23.04.2024 |
| USA: Tallahassee - Singles - Main |
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| 1/16-finals | Hemery C. | Kypson P. | 2:0 (7:62, 6:3) | details | 15.04.2024 |
| USA: Sarasota - Singles - Main |
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| 1/16-finals | Krueger M. | Kypson P. | 2:1 (6:2, 3:6, 7:61) | details | 08.04.2024 |
| USA: Houston - Singles - Main |
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| 1/16-finals | Kypson P. | Bergs Z. | 0:2 (65:7, 3:6) | details | 01.04.2024 |
| USA: Houston - Singles - Qualification |
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| Final | Kypson P. | Holt B. | 0:0 RET. (4:1) | details | 31.03.2024 |
| Semi-finals | Kypson P. | Pannu K. | 2:0 (6:2, 6:2) | details | 30.03.2024 |
| USA: Miami - Singles - Qualification |
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| Semi-finals | Kovacevic A. | Kypson P. | 2:0 (6:2, 7:65) | details | 18.03.2024 |
| USA: Indian Wells - Singles - Main |
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| 1/32-finals | Kypson P. | Humbert U. | 0:2 (4:6, 4:6) | details | 09.03.2024 |
| 1/64-finals | Quinn E. | Kypson P. | 0:2 (1:6, 61:7) | details | 08.03.2024 |
| USA: Delray Beach - Singles - Main |
|---|
| Quarter-finals | Giron M. | Kypson P. | 2:0 (6:4, 6:4) | details | 17.02.2024 |
| 1/8-finals | Lestienne C. | Kypson P. | 0:2 (4:6, 4:6) | details | 14.02.2024 |
| 1/16-finals | Kypson P. | Kecmanovic M. | 2:0 (6:4, 7:63) | details | 13.02.2024 |
| USA: Cleveland - Singles - Main |
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| Final | Kypson P. | Quinn E. | 2:1 (4:6, 6:3, 6:2) | details | 04.02.2024 |
| Semi-finals | Duckworth J. | Kypson P. | 0:2 (3:6, 61:7) | details | 03.02.2024 |
| Quarter-finals | Nava E. | Kypson P. | 1:2 (6:4, 61:7, 4:6) | details | 02.02.2024 |
| 1/8-finals | Cassone M. | Kypson P. | 0:2 (4:6, 64:7) | details | 31.01.2024 |
| 1/16-finals | Ponwith N. | Kypson P. | 0:2 (3:6, 2:6) | details | 30.01.2024 |
 Australia: Australian Open - Singles - Main |
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| 1/64-finals | Kypson P. | Ruusuvuori E. | 1:3 (6:4, 3:6, 4:6, 64:7) | details | 15.01.2024 |
 New Zealand: Auckland - Singles - Qualification |
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| Final | Kypson P. | Tabilo A. | 0:2 (63:7, 3:6) | details | 06.01.2024 |
| Semi-finals | Delaney Ja. | Kypson P. | 0:2 (1:6, 4:6) | details | 05.01.2024 |
| Semi-finals | Daniel T. | Kypson P. | CAN. | details | 05.01.2024 |
 New Caledonia: Noumea - Singles - Main |
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| 1/8-finals | Cazaux A. | Kypson P. | 2:1 (3:6, 7:67, 6:2) | details | 03.01.2024 |
| 1/16-finals | Kypson P. | Mott B. | 2:0 (6:3, 7:5) | details | 02.01.2024 |
| USA: Champaign - Singles - Main |
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| Final | Kypson P. | Michelsen A. | 2:0 (6:4, 6:3) | details | 19.11.2023 |
| Semi-finals | Kypson P. | Quinn E. | 2:0 (6:4, 6:2) | details | 18.11.2023 |
| Quarter-finals | Kovacevic A. | Kypson P. | 1:2 (62:7, 6:4, 3:6) | details | 18.11.2023 |
| 1/8-finals | Miyoshi K. | Kypson P. | 0:2 (3:6, 1:6) | details | 16.11.2023 |
| 1/16-finals | Whitehouse M. | Kypson P. | 0:2 (1:6, 65:7) | details | 14.11.2023 |
| USA: Knoxville - Singles - Main |
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| 1/16-finals | Kudla D. | Kypson P. | 2:1 (65:7, 6:3, 6:4) | details | 07.11.2023 |
| USA: Charlottesville - Singles - Main |
|---|
| Semi-finals | Zhukayev B. | Kypson P. | 2:0 (6:4, 7:64) | details | 04.11.2023 |
| Quarter-finals | Kypson P. | Holt B. | 2:0 (6:1, 6:4) | details | 03.11.2023 |
| 1/8-finals | Kudla D. | Kypson P. | 0:2 (1:6, 3:6) | details | 01.11.2023 |
| 1/16-finals | Kypson P. | Debru G. | 2:0 (6:4, 7:5) | details | 30.10.2023 |
| USA: Fairfield - Singles - Main |
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| 1/16-finals | Kypson P. | Mayo A. | 1:2 (6:3, 63:7, 64:7) | details | 09.10.2023 |
| USA: Tiburon - Singles - Main |
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| 1/16-finals | Galarneau A. | Kypson P. | 2:0 (7:65, 6:4) | details | 03.10.2023 |
| USA: Charleston - Singles - Main |
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| 1/16-finals | Kypson P. | Peniston R. | 0:2 (2:6, 4:6) | details | 27.09.2023 |
| USA: Cary 2 - Singles - Main |
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| Semi-finals | Hijikata R. | Kypson P. | 2:0 (6:4, 6:2) | details | 16.09.2023 |
| Quarter-finals | Kypson P. | Sandgren T. | 2:0 (7:64, 6:3) | details | 16.09.2023 |
| 1/8-finals | Walton A. | Kypson P. | 0:2 (5:7, 3:6) | details | 15.09.2023 |
| 1/16-finals | Kypson P. | Geerts M. | 2:0 (6:1, 6:3) | details | 13.09.2023 |
| USA: US Open - Singles - Qualification |
|---|
| Semi-finals | Kypson P. | Shang J. | 0:2 (4:6, 62:7) | details | 24.08.2023 |
| Quarter-finals | Rodionov J. | Kypson P. | 0:2 (4:6, 4:6) | details | 22.08.2023 |
| USA: Cary - Singles - Main |
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| Semi-finals | Kypson P. | Moreno De Alboran N. | 1:2 (7:610, 3:6, 1:6) | details | 12.08.2023 |
| Quarter-finals | Kypson P. | Wu Tung-Lin | 2:0 (6:3, 7:64) | details | 11.08.2023 |
| 1/8-finals | Hong S. C. | Kypson P. | 0:2 (4:6, 4:6) | details | 10.08.2023 |
| 1/16-finals | Smith K. | Kypson P. | 0:2 (3:6, 2:6) | details | 09.08.2023 |
Canada: Winnipeg - Doubles - Main