#4 Jonathan Woodgate
Following in the footsteps of Bryan Robson, Steve McClaren and current England boss Gareth Southgate, Jonathan Woodgate was given his first managerial job under the watchful eye of Steve Gibson at Middlesbrough.
After an impressive but often injury interrupted career which saw him play for Leeds United, Newcastle United, Real Madrid, Tottenham Hotspur, Stoke City and two spells at Middlesbrough, Woodgate took his first steps into coaching under Tony Pulis, who had replaced previous incumbent Garry Monk.
The football played by Pulis was unpopular and his contract was allowed to expire at the end of the 2018-19 season after his side missed out on the playoffs. Woodgate would replace Pulis, and after appointing Robbie Keane as his assistant, stated his ambition to bring more attractive football back to the club.
Despite much being expected of Woodgate, he experienced a very tough start to life in management with his side having only won two of his first 17 league games in charge, which saw his team firmly rooted in the relegation zone.
This run of form would have seen many chairman get nervous and replace their rookie manager but Gibson is renowned for giving his managers time and he chose to support Woodgate through this difficult period.
This faith appeared justified when Middlesbrough went on a four game winning streak over the Christmas and New Year period, which saw him awarded the Championship Manager of the month award. However a run of four draws and two defeats in the last six games has left them nervously looking over their shoulder, though they are currently seven points clear of trouble.