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: | 2024 | 2023 | 2022 | 2021 | 2020 | 2019 | 2018 | 2017 | 2016 | 2015 | 2014 | 2013 | 2012 | 2011 | 2010 | 2009 | 2008 | 2007 | 2006 | 2005 | 2004 |
| Winter: | 2024 | 2023 | 2022 | 2021 | 2020 | 2019 | 2018 | 2017 | 2016 | 2015 | 2014 | 2013 | 2012 | 2011 | 2010 | 2009 | 2008 | 2007 | 2006 | 2005 |
2018 Winter Challenge Results
| Flight | Pos | Challenger | Flight | Pos | Challengee | Winner | Score |
| 2 | 1 | Connell / Leddy | 1 | 6 | Prochilo / Shonfield | Prochilo / Shonfield | 6-3, 6-3 |
| 2 | 2 | Bergman / Imbruce | 1 | 5 | Fox / Kloud | Bergman / Imbruce | 6-1, 6-4 |
| 3 | 1 | Thomson / Tucker | 2 | 6 | Schmitz / Walker | Thomson / Tucker | 6-4, 6-3 |
| 3 | 2 | Ahrens / Grillo | 2 | 5 | Augustine / Johnson | Augustine / Johnson | 6-2, 6-4 |
| 4 | 1 | Street / Waldron | 3 | 7 | Baldwin / Laughton | Street / Waldron | 6-2, 6-2 |
| 4 | 2 | Root / Tierney | 3 | 6 | Beecher / Hladick | Root / Tierney | default |
| 5 | 1 | Laska / Mitchell | 4 | 7 | Corcoran / Dunn | Laska / Mitchell | default |
| 5 | 2 | Nelson / Yao | 4 | 6 | Discenza / Zoccolillo | Nelson / Yao | 6-2, 6-3 |
| 6 | 1 | Brennan / Finkel | 5 | 8 | Carter / Hering | Brennan / Finkel | default |
| 6 | 2 | Bennett / Benton | 5 | 7 | Oppel / Orteig | Bennett / Benton | 7-6, 6-1 |
| 7 | 1 | Hearle / Laverne | 6 | 7 | Dynan / Ho | Dynan / Ho | 6-0, 6-1 |
| 7 | 2 | Austin / Mason | 6 | 6 | Boshnack / Hott | ||
| W2 | 1 | Norley / Ruggieri | W1 | 6 | Frieders / Sadowski | ||
| W2 | 2 | Moutran / Pearl | W1 | 5 | Graham / Reagan | Graham / Reagan | 7-5, 6-1 |
| W3 | 1 | Maijala / Parrett | W2 | 6 | Ferris / Kerridge | Maijala / Parrett | default |
| W3 | 2 | Brennan / Chalon | W2 | 5 | Carpenter / Ciolli |
Teams highlighted in yellow above are teams involved in ties, see explanations below
| Flight | Pos | Notes |
| 1 | 5 | Fox / Kloud defeated Prochilo / Shonfield to finish 5th |
| 1 | 6 | Prochilo / Shonfield lost to Fox / Kloud to finish 6th |
| 3 | 6 | Beecher / Hladick and Baldwin / Laughton did not play each other, so the first 2 tiebreakers do not apply |
| 3 | 7 | In the3rd tiebreaker, Beecher / Hladick had fewer default losses to finish ahead of Baldwin / Laughton |
| 4 | 1 | In a 3-way tie, Reilly / Tatum, Root / Tierney and Street / Waldron each won 1 matches the other 2 teams |
| In the 2nd tiebreaker, Street / Waldron won 3 sets to finish 1st (the other 2 teams only won 2 sets) | ||
| 4 | 2 | Now we revert back to head-to-head and here Root / Tierney defeated Reilly / Tatum to finish 2nd |
| 6 | 6 | Boshnack / Hott lost to Dinger / Simpson to finish 6th |
| 7 | 1 | Hearle / Laverne defeated Austin / Mason to finish 1st |
| 7 | 2 | Austin / Mason lost to Hearle / Laverne to finish 2nd |
| W1 | 5 | Graham / Reagan defeated Frieders / Sadowski to finish 5th |
| W1 | 6 | Frieders / Sadowski lost to Graham / Reagan to finish 6th |
| W3 | 2 | Brennan / Chalon defeated Azoulay / Lynn to finish 2nd |