#3 Sam Allardyce - 5 times
Sam Allardyce is close to completing 30 years as a football manager. He managed some top English teams like Newcastle United, Blackburn Rovers, Sunderland, Bolton Wanderers, West Ham United, and England national team.
Allardyce was hired as a player-coach at West Bromwich Albion in February 1989 but was later sacked in 1991 after a defeat against Woking in the FA Cup. He managed Blackpool from 1994 to 1996 and was sacked at the end of 1995/96 season.
He managed Bolton for 7 years and then moved to Newcastle where he was sacked within 7 months. He then moved to Blackburn Rovers in 2008. He was sacked by Blackburn in 2010 and then by West Ham United in 2015.
Notably, his role as a manager of England lasted only 67 days, following allegations of malpractice.