In the 1985-86 season Chelsea played in the First Division for the second successive season. It was the first season under the management of John Hollins, who had previously been a member of Chelsea's victories in the 1970 FA Cup Final and 1971 European Cup Winners' Cup Final. On 1 January 1986 Chelsea were second, two points behind leaders Manchester United and in March the club were still in second, four points behind Everton with two games in hand. The two games in hand were lost 4–0 at home to West Ham United and 6–0 away at Queens Park Rangers. After gaining just 9 points from a possible 33 in the last 11 games, Chelsea finished 6th for the second season in succession. On 23 March 1986 Chelsea won the 1986 Full Members Cup Final 5–4 at Wembley Stadium against Manchester City with David Speedie scoring Chelsea's only Wembley hat-trick. Colin Lee scored Chelsea's other two goals. Due to the widespread negativity over English football after the 1985Heysel disaster, victorious manager Hollins was quoted as saying "If football is dying, I hope it's dying like that". After an away win at Shrewsbury Town in the 3rd round of the FA Cup, Chelsea lost 2–1 at home to eventual Champions Liverpool in the fourth round. In the 1985-86 Football League Cup Chelsea beat Mansfield Town in a two-legged second round but required replays to advance past Fulham and Everton in the subsequent rounds. After drawing 1–1 away to Queens Park Rangers Chelsea lost the fifth round replay 2–1 at Stamford Bridge.
Chelsea's kit was produced by Le Coq Sportif for the final of five seasons. The home kit was only worn this season, and re-introduced blue socks in favour of white for the first time since 1967–68. The shirt had shadow-stripes, a popular 1980s style, and the only white was around the v-neck and sleeves. The kit was unsponsored, as it had been since the end of Chelsea's first-ever sponsorship, with Gulf Air in the 1983–84 season. The away kit closely followed the design of the home, but in red with white trim. While the home kit had plain white socks, the red socks of the away kit featured four hoops: a white and blue on both the turnover and the leg. For a third kit, the white away kit from the 1984–85 season was retained. As well as a V-neck, it included red and blue horizontal pinstripes on the shirt and hoops of blue and red on the socks.
