•  Wooster School: Wooster has won the Hudson Valley Athletic League’s most prestigious and highly coveted honor - the Sportsmanship Award - 11 of the last 14 years.

• Sportsmanship Awards: Wooster teams have won 44 sportsmanship awards in the last 17 years.

• League Titles and New England Tournaments: Wooster teams have won 46 league titles and earned 49 bids to the New England tournament in the last 17 years.

• Varsity Girls Soccer: Made it to the HVAL “Hudson Division” Tournament Final Four. This team has been selected to play in the New England tournament 11 times in the past 18 years.

• Varsity Boys Soccer: Made it to the HVAL “Hudson Division” tournament. This team has been selected to play in the New England tournament 6 times in the past 14 years.

• Varsity Girls Volleyball: Made it to the HVAL “Hudson Division” Tournament Final Four. The team made it to the New England tournament 3times in the last 4years. This team has won the HVAL season and tournament championship twice in the last 4 years.

• Coed Cross Country: Finished 3rd out of 10 teams at the HVAL championship meet.

• Varsity Girls Basketball: Made it to the HVAL “Hudson Division” tournament Final Four. This team earned their 18th consecutive bid to the New England tournament, setting a small school New England record. This team has won the HVAL “Hudson Division” season and tournament titles in 12 of the last 18 years, and has won the Ed Costello Holiday Classic 7 times in the past time in the last 9 years.

• Varsity Boys Basketball: Won the HVAL Season title this season and advanced to the New England tournament Finals.

• Varsity Girls Tennis: Made it to the HVAL “Hudson Division” Tournament Semifinals.

• Varsity Boys Tennis: Made it to the "Hudson Division" Tournament Final Four and advanced to the New England tournament for the 9th time in the last 12 years.

• Coed Golf: Earned a 3rd place finish in the HVAL.

• Varsity Boys Baseball: Co-Champions of the HVAL "Valley Division" tournament.

• Varsity Girls Softball: Made it to the HVAL “Hudson Division” tournament Final Four.

• Varsity Girls Lacrosse: Made it to the HVAL “Hudson Division” tournament Final Four. This team has earned the HVAL season and tournament titles 4 times in the last 8 years.

• Varsity Boys Lacrosse: Made it to the HVAL “Hudson Division” tournament Final Four, earned a 2nd place finish in the HVAL, earned a 4th place finish in all of Division III.

• Ultimate Frisbee: Made it to the HVAL “Valley Division” tournament finals for a second consecutive season - and posted its first winning record.