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Alex Fitzgerald had a standout day for Windham in a four-team meet in Concord, carving 48 seconds off his previous career best time and placing as one of the Jaguars' top three finishers for the first time ever. Brandon Bielinski also had a personal best time while Kyle Carbonneau registered his best time of the season.

In the last home meet of their careers, both Colby Putnam and Travis Sanders did well as Windham beat Bishop Brady and fell to Trinity. Putnam registered his best home-course time ever by a whopping 30 seconds, placing first overall in 18:30. Sanders, recovering from a foot injury, ran a season-best 25:15. Freshman Brandon Bielinski continued his consistent running, bettering his best time by six seconds.

With three of the top four finishers, St. Thomas Aquinas won the 15-team Jamie Martin Invitational at Sanborn Regional. Steven Hammar and Brandon Hannon helped Pelham place second, while Colby Putnam chopped 30 seconds from his personal best as Windham's top finisher. Shane Waters was the leading runner for the host school.

Tropical Storm Irene caused trees and branches to fall on Windham's cross country course and a rerouting for its season-opening quad meet. Due to a better sixth-place finisher (Justin Manter), the Jaguars won a tiebreaker over ConVal to finish second behind Hollis-Brookline. Colby Putnam was third overall for Windham, while fourth-place Sanborn was led by Shane Waters.