SEASON: Winter 1996-1997
HEAD COACH: Thomas S. Foster
ASSISTANT COACH: Ned Gallagher
CAPTAIN: Kenneth Woo '97
| DATE | OPPONENT | SITE | TIME | SCORES | NOTES | |
| CRH | OPP. | |||||
| 11-23-96 | Western New England Play Day | home | 1:30 | |||
| 12-7-96 | Phillips Academy | Andover, MA | 4:15 | Match cancelled due to inclement weather. | ||
| 12-7-96 | Phillips Exeter Academy | Andover, MA | 4:15 | Match cancelled due to inclement weather. | ||
| 12-11-96 | Kent School | home | 3:00 | 7 | 0 | |
| 12-14-96 | Loomis Chaffee School | home | 2:30 | 7 | 0 | |
| 12-16-96 | Yale University JV | New Haven, CT | 4:00 | Scrimmage; no score. | ||
| 12-17-96 | Brunswick School | Southport, CT | 3:30 | 2 | 5 | |
| 1-8-97 | Taft School | Watertown, CT | 3:00 | 0 | 7 | |
| 1-11-97 | Choate Rosemary Hall Invitational Team Tournament |
home | 10:00 | 0 | 5 | vs. Episcopal Academy (unofficial match) |
| 2 | 3 | vs. Milton Academy (unofficial match) |
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| 0 | 5 | vs. Taft School (unofficial match) |
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| 5 | 0 | vs. The Hill School (unofficial match) |
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| 1-15-97 | Blair Academy | Millbrook, NY | 3:30 | 3 | 4 | |
| Millbrook School | Millbrook, NY | 5:00 | 7 | 0 | ||
| 1-18-97 1-19-97 |
Choate Junior Squash Championships (USSRA Tournament) |
home | 9:30 | |||
| 1-22-97 | Hotchkiss School | Lakeville, CT | 3:30 | 5 | 2 | |
| 1-25-97 | Milton Academy | home | 1:00 | 4 | 3 | |
| Phillips Academy | home | 5:00 | 4 | 3 | ||
| 1-27-97 | Greens Farms Academy | home | 4:30 | 5 | 2 | |
| 1-29-97 | Trinity-Pawling School | Pawling, NY | 2:30 | 7 | 0 | |
| 2-5-97 | Taft School | home | 3:00 | 0 | 7 | |
| 2-11-97 | Yale University JV | New Haven, CT | 4:00 | Scrimmage; no score. | ||
| 2-12-97 | Avon Old Farms School | home | 3:00 | 7 | 0 | |
| 2-13-97 | Hartford Golf Club Men's Team |
West Hartford, CT | 5:00 | 5 | 4 | |
| 2-14-97 | Westminster School | Simsbury, CT | 3:00 | 2 | 5 | |
| 2-15-97 2-16-97 |
Hartford Golf Club Juniors (USSRA Tournament) |
West Hartford, CT | 3:00 | Choate's #1 Ken Woo '97 and #4 Austin Clark '98 advanced to the semifnals of the Boys Under 19s division. Clark finished in 3rd place. | ||
| 2-19-97 | Deerfield Academy | Deerfield, MA | 3:30 | 4 | 3 | |
| 2-22-97 2-23-97 |
New England Interscholastic Squash Championships |
Trinity College Hartford, CT |
9:00 | Choate's Austin Clark '98 finished as runner-up in the #4 flight and Dan Sigai '97 advanced to the semifinals of the #5 division. The team finished in 7th place among 31 competing schools. Choate also received the Team Sportsmanship Award for the fourth time in five years. | ||
| 3-8-97 | Chipping Norton School | GREAT BRITAIN | 5:00 | 6 | 3 | |
| 3-9-97 | Cheltenham College | GREAT BRITAIN | 3:30 | 4 | 4 | |
| 3-11-97 | Harrow School | GREAT BRITAIN | 3:30 | 4 | 5 | |
| 3-12-97 | Charterhouse | GREAT BRITAIN | 3:00 | 6 | 3 | |
| 3-13-97 | Lancing College | GREAT BRITAIN | 8:00 | 2 | 8 | |
| 3-14-97 | Brighton and Hove VI Form |
GREAT BRITAIN | 4:00 | 7 | 2 | |
| 3-15-97 | Eton College | GREAT BRITAIN | 4:00 | 3 | 6 | Choate last met Eton in squash when an Etonian squad toured the the States in the spring of 1992. |
| 3-16-97 | Wellington College | GREAT BRITAIN | 3:30 | 8 | 1 | |
| 3-17-97 | Cranleigh School | GREAT BRITAIN | 4:00 | 9 | 0 | Choate offers a Term-in-Britain program every fall which is based at Cranleigh School. |
| 16 wins, 8 losses, 1 tie | ||||||
SEASON: Winter 1996-1997
COACH: W. Thomas Generous, Jr.
ASSISTANT COACH: Ned Gallagher
| DATE | OPPONENT | SITE | TIME | SCORES | NOTES | |
| CRH | OPP. | |||||
| 12-7-96 | Taft School | Watertown, CT | 3:00 | 3 | 7 | |
| 12-11-96 | Williston Northampton School Varsity | home | 3:00 | 5 | 5 | |
| 12-14-96 | Avon Old Farms School | home | 2:30 | 5 | 2 | |
| 12-14-96 | Loomis Chaffee School | home | 3:30 | 7 | 0 | |
| 12-17-96 | Brunswick School | home | 4:30 | 5 | 2 | |
| 1-8-97 | Canterbury School Varsity | home | 4:00 | 9 | 0 | |
| 1-13-96 | Brunswick School | home | 4:00 | 3 | 4 | |
| 1-15-97 | Deerfield Academy | Deerfield, MA | 3:15 | 1 | 6 | |
| 1-18-97 1-19-97 |
Choate Junior Squash Championships (USSRA Tournament) |
home | 1:00 | |||
| 1-22-97 | Kingswood-Oxford School Varsity | home | 2:30 | 7 | 0 | |
| 1-25-97 | Williston Northampton School Varsity | Easthampton, MA | 3:00 | 5 | 3 | |
| 1-29-97 | Trinity-Pawling School | Pawling, NY | 4:00 | 4 | 3 | |
| 2-5-97 | Taft School | home | 3:00 | 4 | 3 | |
| 2-12-97 | Hotchkiss School | Lakeville, CT | 3:30 | 6 | 1 | |
| 2-14-97 | Westminster School | Simsbury, CT | 4:00 | 6 | 1 | |
| 2-15-97 2-16-97 |
Hartford Golf Club Juniors (USSRA Tournament) |
West Hartford, CT | 3:00 | Choate's David Pinciss '99 advanced to the semifinals of the Boys Under 16s division. | ||
| 2-19-97 | Deerfield Academy | home | 3:30 | 5 | 2 | |
| 11 wins, 3 losses, 1 tie | ||||||