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.
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He was selected for the squad that went to the 1990 FIFA World Cup in Italy, but his only appearance came on 20 June against Brazil at the Stadio delle Alpi Turin, a game the Scots lost 1–0.
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On 23 August 1994 he returned to Coventry City on a free transfer, making three Premier League appearances during the 1994–95 season.
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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.
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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.
Dizzy Gillespie | Gary Cooper | Gary Moore | Gary Allan | Gary Gygax | Gary, Indiana | Gary Burton | Gary Lineker | Gary Player | Gary Numan | Gary Hart | Gary Snyder | Gary Cole | Gary Busey | Gary Panter | Gary Oldman | Gary Paulsen | Gary Sinise | Gary Johnson | Gary Hughes | Gary Brooker | Gary | Gary Valenciano | Gary Peacock | Gary Owens | Gary Locke | Gary Husband | Gary Graffman | Gary Gilmore | Gary Condit |