Liverpool
Gillespie took a while to settle in, mainly because world-class defenders Mark Lawrenson and Alan Hansen were ahead of him, but eventually he got into the team, making his debut on 7 April 1984 in the 2–2 League Cup draw with Walsall at Anfield, he became a regular during the 1986–87 season. He had played 14 times in the 1985–86 season, however, scoring three league goals, as the Reds sealed the double of the league title and the FA Cup, beating their local rivals Everton into second place and also defeating them 3–1 in the Wembley final. Gillespie did play enough games to warrant a league title winner's medal, but did not make the squad for the FA Cup final.
His first goal had come on 20 April in the 3–1 league win over Newcastle United at Anfield. He remained a mainstay and was part of the side which won the "double" of League championship and FA Cup in 1986, though he missed out on a place in the FA Cup final at a time when only one substitute was permitted.
His three goals in that double winning season all came in the same game. Hat-tricks have always been rare for defenders, but Gillespie managed one against Birmingham City on 26 April 1986 at Anfield, he scored a brace from open play and completed the threesome with a penalty after the Liverpool fans chanted his name when it was awarded – normally he would not have taken it. Liverpool won the game 5–0 against an already relegated side, as they moved closer to title glory (which was sealed on the final day of the season with a 1-0 win at Chelsea).
Gillespie firmly established himself in the first team the following year, when he missed just three league games all season. By 1988, when he partnered Hansen in all bar five of Liverpool's games in the league, the Anfield club were a cut above every other side, losing just twice and coasting to the title. Gillespie weighed in with his share of goals too, including one in the famous 5–0 hammering of Nottingham Forest, which critics, including the great Tom Finney, describe to this day as the finest domestic performance by any English club.
A week before Liverpool were scheduled to face Wimbledon in the FA Cup final to try to secure their second "double", Gillespie and teammate Nigel Spackman clashed heads when leaping for the same ball in a league game against Derby County. Both suffered deep cuts, but were deemed fit for the game at Wembley and were each given customised protective bandages with red and white stripes to wear during the game. Gillespie was regarded as one of Liverpool's better players on the day. BBC summariser Jimmy Hill said: "Gillespie's been brilliant, headband or not," but Liverpool surprisingly lost 1–0.
In April 1989, Gillespie joined his teammates in mourning the death of 94 Liverpool fans (the final death toll was 96) at the Hillsborough disaster, during a year in which he again was a regular feature in the team. This time fortunes were reversed – Liverpool won the FA Cup with an emotional victory over fierce Merseyside rivals Everton, but lost the League title to Arsenal with pretty much the last kick of the season. Gillespie missed that game, however.
Gillespie won another league title with Liverpool in 1990, though his appearances record was diminishing, owing to the arrival of Swedish defender Glenn Hysen at Anfield. However, he still managed four goals from a mere 13 league games.
In 1990–91, with the absence and eventual retirement of Alan Hansen due to injury, Gillespie was once again a regular in the centre of the Anfield defence. He played 30 league games and scored once, remaining a regular player even after the resignation of Kenny Dalglish as manager on 22 February 1991 – after which he was succeeded by Graeme Souness.
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