Gillespie stayed at Newcastle for three-and-a-half years and during this time he played 143 games, including 15 European ties (in both the Champions League and UEFA Cup) and scored 13 goals. In both the 1995–96 and 1996–97 seasons he helped Newcastle to finish second in the Premier League (runners up to Gillespie's former club, Manchester United, on both occasions), being a key member of "The Entertainers". On the first occasion, the Magpies very nearly beat Gillespie's old club to the title, having been 10 points ahead of them by Christmas 1995 before a dismal final three months of the season saw the title sealed by Gillespie's former team mates. Initially injured from a Phil Neville tackle in a 0–2 defeat at Old Trafford on 27 December 1995 causing him to miss the following three games, at the end of the 1995–96 season Gary Lineker, then a BBC pundit, said that one of the main reasons that Newcastle lost out on the title race was because they dropped Gillespie (who had been supplying Newcastle's forwards with a stream of good crosses) for several key games in the latter part of the season.