3) Pep Guardiola (Manchester City) – 5 Years And 229 Days

Guardiola

The Spaniard is in his longest spell in management at any team and, with the resources at his disposal, why would he go anywhere else?

Guardiola may have spent big in the transfer market since his arrival at the Etihad but he has backed that up with huge success on the pitch, winning ten major trophies.