1986–87 Gillingham F.C. season

The 1986–87 season was the fifty-fifth season in which football club Gillingham F.C. competed in the Football League, and the thirty-seventh since the club's return to the League in 1950. Gillingham finished the season in fifth place in the Football League Third Division, thus qualifying for the play-offs in the first year in which they were contested. After beating Sunderland in the semi-finals, the Gills faced long-time rivals Swindon Town in the final. The two teams drew 2–2 on aggregate in the final, necessitating a play-off at a neutral venue, which Swindon won 2–0 to claim a place in the Second Division.^[1] Gillingham also reached the third round of the FA Cup and the semi-finals of the Associate Members' Cup.^[1]

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