In 1996–97, Robson led Boro to both domestic cup finals, but they were on the losing side both times, losing 1–0 in a replay to Leicester City in the League Cup Final replay and 2–0 in the FA Cup Final to Chelsea, while they suffered relegation in the Premier League. However, this relegation would have been avoided if they had not been deducted three points in mid-season for cancelling a fixture at late notice due to many players being unfit through illness or injury. However, at least Boro had the consolation of staying alive in the league up to the last day of the season. Boro were already bottom of the league at the turn of 1997, but when the points were deducted they found themselves seven points adrift of safety with the 17th placed team having a game in hand. However, results slowly improved over the next few weeks and by the end of March a succession of good results had seen Boro climb out of the relegation zone. This, coupled with the excellent cup runs, saw Robson voted Premier League Manager of the Month for March 1997. Robson made one playing appearance this season on New Years Day, starting in a 2–0 defeat away to Arsenal. This proved to be his last game as a professional footballer, though he did not announce his retirement from playing until later in the season.