Martin O’Neill
League Cup Status – Winner (Leicester city) 1997, 2000. Runner Up 1999

O’Neill is one of the greatest managers in British football history. He was appointed manager in 1995 and started a remarkable period for the club. He led them to victory in the 1997 league cup with a win in the final over Middlesbrough and the 2000 league cup final against Tranmere. Leicester were also runner up in the 1999 league cup final as they lost 1-0 to Spurs. In his first season at the club he helped them to promotion into the premiership. He eventually left Leicester City to take charge of Celtic in Scotland. In the summer of 2006 he was appointed manager of Aston Villa.

Brian Clough
League Cup Status – Winner (Nottingham Forest) 1978, 1979, 1989, 1990. Runner Up 1980, 1992
Clough was arguably the greatest manager ever in English football. He made Nottingham Forest into the best club in the world during the late 1970’s.
In total Clough managed Forest to success in four league cups; he won the European Cup with Forest in the 1978- 79 season. He took them to the brink of FA Cup success in the 1991 as they lost to Tottenham in the final 2-1.
In total Clough spent 18 years managing Nottingham Forest. Before managing Forest he had spells in charge of Brighton, Leeds United, Hartlepool and Derby County. His son, Nigel, is currently managing Burton Albion football club.

Bruce Rioch
League Cup Status – Runner up (Bolton) 1995
Rioch took Bolton to the brink of success in the league cup in 19995. However his team heroically lost 2-1 to Liverpool. He was installed as Bolton manager in 1992 and guided them to promotion to the premiership during the 1994-95 season. His brilliance at Bolton lured him a move to Arsenal at the beginning of the 1994- 95 season. He has also managed Torquay, Middlesbrough, Mill Wall and Wigan.