Sir Bobby Robson | Newcastle United | September 1999 - August 2004
Taking over the club at the start of the 1999-2000 campaign, Sir Bobby Robson helped Newcastle raise to the top of the table, including a fourth place finish in the 2002-03 season and third place in the 03-04 season.
Also during his 1815 day stint, he secured a place in the champions league twice, reaching the second group stage in 02-03.
Jim Smith | Derby County | August 1996 - October 2001
Jim Smith led Derby County to promotion to the Premier League in the 95-96 season and kept them there throughout his entire 1877 days at the helm, securing two top-half finishes in the club's first three years in the top division. He resigned at the beginning of the 01-02 season in which Derby were later relegated.
Gerard Houllier | Liverpool | November 1998 - May 2004
Initially Gerard Houllier joined Liverpool as joint-manager with Roy Evans before becoming the sole boss just a few months later and for the next 2018 days. During his stint he earned the cup treble in 01-02 and led Liverpool to a second-place finish the next season.
Sam Allardyce | Bolton Wanderers | August 2001 - April 2007
Sam Alladyce is no stranger to the Premier League having been manager of six clubs all in the top division and is the current boss of Everton. However, his longest spell is while manager of Bolton Wanderers who he led to promotion to the Premier League in the 00-01 season and where they remained for Alladyce's full 2079 days in charge.
Alan Curbishley | Charlton Athletic | August 2000 - May 2006
While manager at Charlton, Alan Curbishley led the club to the Premier League twice - first in 1998 and then again in 2000. Curbishley's exit from the club coincided with their relegation in the 05-06 season, with Charlton having failed to return to the Premier League since.
Rafael Benitez | Liverpool | August 2004 - June 2010
Despite being the current Newcastle manager Rafael Benitez's first stint in the Premier League was with Liverpool. During his 2119 days at the club he saw them reach two Champions League finals and get close to winning the league in 2009. He left in 2010 to join Serie A side Inter.
Harry Redknapp | West Ham United | August 1994 - May 2001
Harry Redknapp's first spell as a Premier League manager began at the beginning of the 94-95 season with West Ham United. During his 2454 days at West Ham he saw them finish in fifth place and win the UEFA Intertoto Cup resulting in qualification for the UEFA cup the following year.
David Moyes | Everton | March 2002 - May 2013
Moyes spent 11 seasons at Everton totalling 4082 days and resulted in him being named LMA Manager of the year three times after finishing in the top ten in nine of his seasons in charge. He left in 2013 to take over Manchester United.
Sir Alex Ferguson | Manchester United | August 1992 - May 2013
Up until 2018, Sir Alex Ferguson held the title of longest serving Premier League manager having overseen Man Utd since the Premier League began in 1992 and saw them lift the first Premier League trophy. He then led the team to multiple domestic and international cups before retiring in May 2013.
Arsene Wenger | Arsenal | October 1996 - May 2018
Arsene Wenger called time on his spell as Arsenal manager in May 2018, bringing to an end his 22-year stint in charge.
The Frenchman enjoyed instant success with the Gunners - leading them to the Premier League and FA Cup double in 97-98 - as well as building the famous 03-04 Invincibles side which won the league.
Wenger won three Premier League titles and seven FA Cups in total as Arsenal manager.
