Following the departure of the Northeast League's Sullivan Mountain Lions after one season in Mountaindale, the Cougars played their home games at Baxter Stadium, and were part-owned by comedian Bill Murray.
They left Mountaindale after only one season and, under new ownership, were replaced by Catskill Cougars, a new team in the year-old North Atlantic League.
In their first season, the Cougars boasted the NAL's second-best offense, but also its second-worst pitching staff; they were actually outscored in their league games.
The Cougars then stunned the Mad Dogs by sweeping the best-of-three title series, two games to none, becoming the first pro baseball team based in Sullivan County to win a championship.
The team featured former major-leaguers Vance Lovelace, Kerwin Moore, and Matt Murray.
But prior to the start of the 2000 season, the Massachusetts Mad Dogs ran into financial trouble and folded.