Just the second softball team to go into the KSC Hall of Fame, the 1999 group set a then school-record for wins (33) and won the programs' first LEC regular season and tournament championships, reaching the final of the NCAA Division III Northeast Regional. Led by future Hall of Famers Carrah Fisk '99, Kara Suhie '99, and Lindsey Blood '00, the Owls captured the first LEC regular season championship with a 13-1 mark in conference play.
Hosting the LEC tournament championship, the Owls rolled through UMass Boston, Eastern Connecticut State, and Western Connecticut State twice by a combined score of 29-4 to reach the NCAA tournament for the first time since 1994. Sent to Ithaca, N.Y., the Owls defeated SUNY Oneonta and Western Connecticut State again before bowing out to Ithaca, finishing as the NCAA Regional runner-up.
Keene State was all over the awards that spring; Fisk was named LEC Player of the Year, while Blood was named LEC Pitcher of the Year. Head Coach Charlie Beach was chosen as the LEC Coach of the Year, and Beth Ponte was named the LEC Tournament's Most Outstanding Player. Ponte, Fisk, Blood, Suhie, Erin Van Nostrand, and Kirsten Bailey were all picked as First Team All-LEC Players, and Bonny Young was named Honorable Mention All-LEC. Suhie was chosen as a Second Team All-American and a First Team All-Region. Fisk and Blood were also named as First Team All-Region. Ponte was a Second Team All-Region choice, and Bailey was a Third Team All-Region selection.