Wurtenburg scheduled a thirteen-game season for 1895, a still-standing record at Dartmouth for most games played in a single year. The team went 7–5–1, which included a 2–0 record against Triangular Football League opponents. The season began with a 50–0 shutout of Phillips Exeter Academy, which was followed by a close game with Harvard. The match was hard-fought; Harvard won by a slim 4–0 margin, the closest that a Dartmouth team had gotten to beating Harvard. The squad then played three smaller colleges, winning two of the games and tying the other. The team then went back-and-forth between losing and winning, falling twice to Yale and once to West Point, but defeating MIT and Boston. Conference opponents Williams and Amherst were defeated by a combined score of 30–5, and the team was awarded its third straight Triangular Football League championship. The season ended on a negative note, however, with a close 10–4 loss to Brown.