| TT Cup | 02/22 03:05 | - | Gary Osmanoff v Preston Stecklein | L | 0-3 | |
| TT Cup | 02/22 02:35 | - | Gary Osmanoff v Brad Robbins | L | 0-3 | |
| TT Cup | 02/22 02:05 | - | Gary Osmanoff v Preston Stecklein | W | 3-2 | |
| TT Cup | 02/22 01:35 | - | Gary Osmanoff v Don Ange Cedric Oba | L | 1-3 | |
| TT Cup | 01/04 03:00 | - | Gary Osmanoff v Abhishek Dhawan | L | 2-3 | |
| TT Cup | 01/04 02:30 | - | Gary Osmanoff v Abhishek Dhawan | W | 3-1 | |
| TT Cup | 01/04 02:00 | - | Gary Osmanoff v Rana Gaurang | L | 0-3 | |
| TT Cup | 01/04 01:30 | - | Gary Osmanoff v Rich Dewitt | L | 2-3 | |
| TT Cup | 12/14 03:00 | - | Gary Osmanoff v Rana Gaurang | L | 2-3 | |
| TT Cup | 12/14 02:30 | - | Gary Osmanoff v Rana Gaurang | W | 3-1 | |
| TT Cup | 12/14 02:00 | - | Gary Osmanoff v Artur Cohen | L | 1-3 | |
| TT Cup | 12/14 01:30 | - | Gary Osmanoff v Enrique Orollano | L | 1-3 | |
| TT Cup | 11/30 03:05 | - | Alex Averin v Gary Osmanoff | L | 3-0 | |
| TT Cup | 11/30 02:30 | - | Gary Osmanoff v Praj Gandhi | W | 3-2 | |
| TT Cup | 11/30 02:00 | - | Gary Osmanoff v Rana Gaurang | W | 3-2 | |
| TT Cup | 11/30 01:30 | - | Gary Osmanoff v Alex Averin | L | 1-3 | |
| TT Cup | 11/16 03:05 | - | Gary Osmanoff v Praj Gandhi | W | 3-2 | |
| TT Cup | 11/16 02:30 | - | Gary Osmanoff v Praj Gandhi | W | 3-2 | |
| TT Cup | 11/16 02:00 | - | Gary Osmanoff v Preston Stecklein | W | 3-0 | |
| TT Cup | 11/16 01:30 | - | Gary Osmanoff v Rana Gaurang | L | 0-3 | |
| TT Cup | 11/09 03:05 | - | Praj Gandhi v Gary Osmanoff | L | 3-0 | |
| TT Cup | 11/09 02:35 | - | Praj Gandhi v Gary Osmanoff | L | 3-1 | |
| TT Cup | 11/09 02:05 | - | Gary Osmanoff v Rana Gaurang | W | 3-0 | |
| TT Cup | 11/09 01:30 | - | Preston Stecklein v Gary Osmanoff | W | 2-3 | |
| TT Cup | 10/12 02:05 | - | Gary Osmanoff v Rana Gaurang | L | 0-3 | |
| TT Cup | 10/12 01:30 | - | Gary Osmanoff v Rana Gaurang | W | 3-1 | |
| TT Cup | 10/12 01:00 | - | Gary Osmanoff v Simon Shtofmakher | W | 3-0 | |
| TT Cup | 10/12 00:30 | - | Gary Osmanoff v Sanjay Jain | W | 3-1 | |
| TT Cup | 07/27 01:00 | - | Gary Osmanoff v Michael Zhang | W | 3-1 | |
| TT Cup | 07/27 00:30 | - | Gary Osmanoff v Enrique Orollano | W | 3-2 |