Middlesbrough have flirted with Championship play-off success in the last two seasons. Steve Gibson has watched his Boro side struggle in their fight for promotion over the past seven years. Middlesbrough finished second in the Championship under Aitor Karanka in 2015/16, earning a place in the Premier League. However, the Teessiders were relegated back down to the second division after just one year in the top flight. Since returning to the Championship, a plethora of managers including Tony Pulis, Neil Warnock, and Chris Wilder have tried and failed to win promotion with the club. Boro finis…