Matt Gillies guided Leicester City to two FA Cup finals in the early 1960’s, suffering defeat against Tottenham Hotspur in the 1961 final and defeat against Manchester United in the 1963 FA Cup final. Leicester City achieved their finest achievement in the year 1964 as they won the league cup. They defeated Stoke City by 4-3 on aggregate in the final and repeated their great play in the competition the following season as they reached the final, however this time suffered defeat against Chelsea in the 1965 league cup final.
Gillies spent nine years in charge at Leicester City before leaving in 1968 as Frank O’Farrell took charge at the club. The Foxes reached the quarter finals of the FA cup in 1968, however suffered a narrow defeat against Everton in the last eight.
The Foxes reached their fifth domestic cup final in eight years in 1969 as they enjoyed a great run in the FA Cup that saw the Foxes reach the final where they met Manchester City in the final. In a final that is remembered as the ‘cabbage patch final,’ because of the poor state of the pitch, they were defeated 1-0 against Manchester City. It was a season which Leicester City also suffered relegation out of the top flight.