Click on the years below to see past results. Please note the 2012 Fall challenges were cancelled due to Super Storm Sandy and the 2020 Fall challenges were cancelled due to COVID 19.
| Fall: | '24 | '23 | '22 | '21 | '20 | '19 | '18 | '17 | '16 | '15 | '14 | '13 | '12 | '11 | '10 | '09 | '08 | '07 | '06 | '05 | '04 |
| Winter: | '25 | '24 | '23 | '22 | '21 | '20 | '19 | '18 | '17 | '16 | '15 | '14 | '13 | '12 | '11 | '10 | '09 | '08 | '07 | '06 | '05 |
2005 Winter Challenge Results
| Flight | Pos | Challenger | Flight | Pos | Challengee | Winner | Score |
| 2 | 1 | Hoelzer / Sloan | 1 | 8 | Bromberg / Sweeney | Bromberg / Sweeney | 6-1, 6-7, 6-2 |
| 2 | 2 | Snelling / Ward | 1 | 7 | Jonker / Ross | Jonker / Ross | 6-2, 6-2 |
| 3 | 1 | Duhamel / Neuhaus | 2 | 8 | Miller / Wrenn | Miller / Wrenn | 6-4, 6-3 |
| 3 | 2 | Ceresa / Mueller | 2 | 7 | Stewart / Tabah | Stewart / Tabah | default |
| 4 | 1 | Majors / Sheehy | 3 | 7 | Bongaerts / Lesko | Majors / Sheehy | default |
| 4 | 2 | DiRubio / Ondash | 3 | 6 | Evans / Krohley | DiRubio / Ondash | 6-4, 1-6, 7-6 |
| 5 | 1 | Kloud / Lavieri | 4 | 8 | O’Neil / Swan | O’Neil / Swan | default |
| 5 | 2 | Heilbron / Keneally | 4 | 7 | Kelly / Wyman | Heilbron / Keneally | 7-5, 6-4 |
| 6 | 1 | Hays / Hood | 5 | 8 | McMillan / Slemp | Hays / Hood | default |
| 6 | 2 | Johnson / Martin | 5 | 7 | Belodeau / Stanley | Johnson / Martin | 6-1, 6-4 |
| 7 | 1 | Aliapoulios / McIntyre | 6 | 8 | Benko / Mallozzi | Aliapoulios / McIntyre | default |
| 7 | 2 | Ferarro / Moreno | 6 | 7 | Corcoran / Higgins | Ferarro / Moreno | 6-4, 6-0 |
| 8 | 1 | Gesing / Rigo | 7 | 8 | Swanberg / Taddonio | Gesing / Rigo | 6-1, 6-1 |
| 8 | 2 | Faughnan / Willett | 7 | 7 | Jodka / Turner |