5) Arsene Wenger – Arsenal
If you ignore the last 10 years it is evident that Arsene Wenger was accustomed to winning trophies between 1997 and 2002.
That successful period saw the Frenchman guide the Gunners to a pair of Premier League and FA Cup doubles in 1998 & 2002 meaning it’s also four trophies in the first five full seasons for the experienced manager too.