Carlo Ancelotti
Player: Milan (1990)
Coach: Milan (2003, 2007), Real Madrid (2014)
- Beat Sampdoria as a player, before one victory against Porto and two against Sevilla as a coach.
Diego Simeone
Player: Lazio (1999)
Coach: Atlético Madrid (2012)
- Both wins came against English clubs, Manchester United dispatched by Lazio and Chelsea vanquished by a Radamel Falcao-inspired Atlético.
Josep Guardiola
Player: Barcelona (1992)
Coach: Barcelona (2009, 2011), Bayern München (…