The 2008-09 team earned an overall 5th Place finish out of 19 teams in the Big East Confernece's Regional Tournament held on February 1, 2009. Of the 31 Westford wrestlers participating in the Regional tournament, 26 wrestlers placed in the top three of their respective divisions, with 4 winning 1st place honors. Placewinners included:
Novice Division
1st Place - Dan Regan, Brennon Butler and Jack Quaranto
2nd Place - Will Puduski, Kevin Keins and John McGrath
3rd Place - Connor Barry, Cole Barnshaw, Tyler Bella, Cooper Hart, Connor McDonough, Andrew Piedrahita, Dan Wilson and Kenny Tashjy
Select Division
1st Place - Thomas Sherriff
2nd Place - Kyle Giliberti, Keaton Solo, Nick Regan and Ian Lobo
3rd Place - Ryan Hopkins and Greg Sargeant
Elite Division
1st Place - Nate Tashjy
2nd Place - Mike Murphy and Danny Cerullo
3rd Place - Evan Monoxelos