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In 1986, the Republic of Ireland appointed Jack Charlton, a top rated English manager who had been part of England's World Cup-winning side of 1966. During the 1970s, he had developed Middlesbrough into a side which provided many players to the dominant Liverpool team of the time.

After taking charge of the Republic of Ireland, Charlton influenced changes in the national side which resulted in their most successful period of its history, qualifying for two World Cups and a European Championship.

Ireland's first appearance at a major finals tournament came in Euro 1988. With Ireland's fixtures already complete, qualification was secured through Gary Mackay's 87th-minute goal in Sofia when Scotland beat Bulgaria 1–0; the Scottish win left Ireland top of the group. In the finals in West Germany, Ireland shocked Europe by beating England 1–0 in Stuttgart with a header from Ray Houghton in their competitive debut; drew 1–1 with the Soviet Union in Hannover, with Ronnie Whelan the scorer; and lost to eventual champions the Netherlands 1–0 in Gelsenkirchen, coming within seven minutes of a draw that would have meant a semi-final place.