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 |
2016 Winter Challenge Results
| Flight | Pos | Challenger | Flight | Pos | Challengee | Winner | Score |
| 2 | 1 | Mohr / Murphy | 1 | 7 | Eccleston / Scanlon | Mohr / Murphy | default |
| 2 | 2 | Morse / Russo | 1 | 6 | Gesing / Van Ess | Gesing / Van Ess | 6-4, 6-3 |
| 3 | 1 | Hanratti / Imbruce | 2 | 7 | Baldwin / Laughton | Hanratti / Imbruce | 6-3, 4-6, 6-3 |
| 3 | 2 | Sibbett / Wheeler | 2 | 6 | Prochilo / Shonfield | Prochilo / Shonfield | 6-1, 6-3 |
| 4 | 1 | Deligtisch / Stallings | 3 | 7 | Beecher / Hladick | Deligtisch / Stallings | 6-0, 6-1 |
| 4 | 2 | Brown / Howe | 3 | 6 | Burns / John | Brown / Howe | 6-2, 6-2 |
| 5 | 1 | Bazata / Castiglione | 4 | 8 | Gillen / Hering | Bazata / Castiglione | default |
| 5 | 2 | Corcoran / Dunn | 4 | 7 | Schmitz / Walker | Schmitz / Walker | 7-5, 6-7, 7-5 |
| 6 | 1 | Sanders / Smith | 5 | 7 | Finnigan / Wise | Sanders / Smith | default |
| 6 | 2 | Skidmore / Tobin | 5 | 6 | Haussler / McLaughlin | Skidmore / Tobin | 6-1, 6-2 |
| 7 | 1 | Norton / Overacker | 6 | 7 | Mijne / Siegel | Norton / Overacker | default |
| 7 | 2 | Hetherington / Koller | 6 | 6 | Abbott / Negley | Hetherington / Koller | 7-5, 6-3 |
| 8 | 1 | Mitchell / Warren | 7 | 7 | Rechtermann / Schneider | Mitchell / Warren | default |
| 8 | 2 | Howarth / Moor | 7 | 6 | Mazabras / Murray | Howarth / Moor | 7-5, 6-2 |
| W2 | 1 | Ahrens / Schmitz | W1 | 6 | Cannon / Morgan | Ahrens / Schmitz | 6-2, 6-2 |
| W2 | 2 | Sousa / Vives | W1 | 5 | Dinning / Van de Graaf | Sousa / Vives | 4-6, 6-1, 6-0 |
| W3 | 1 | Thomson / Tucker | W2 | 6 | Banford / Frieders | Thomson / Tucker | default |
| W3 | 2 | Rosen / Stevenson | W2 | 5 | Smicka / Steele | Smicka / Steele | 6-4, 6-2 |
Teams highlighted in yellow above are teams involved in ties, see explanations below
| Flight | Pos | Notes |
| 3 | 2 | Sibbett / Wheeler defeated Blair / Warner to finish 2nd |
| 3 | 6 | Burns / John lost to Heron / Parrott to finish 6th |