Leadbitter is no stranger to play-off campaigns both during his time at the Riverside and upon his return to Sunderland.
The midfielder led Boro out in the defeat to Norwich City in the 2015 final at Wembley Stadium before being an unused substitute for Tony Pulis in both semi-final ties against Aston Villa three years later.
Leadbitter headed back to the Stadium of Light in 2019 where he would be on the losing side at Wembley once more as the Black Cats missed out on a return to the Championship against Charlton Athletic before last season’s semi-final defeat to Lincoln City.
Leadbitter, 36, called time on his playing career by officially announcing his retirement back in September after he left the Stadium of Light but remains an interested supporter of both North East teams who he represented.
Leadbitter spent six years on Wearside before moving to Ipswich Town in 2009 but would return to the North East in 2012 where he would spend almost seven years on Teesside before that switch back to the Stadium of Light where he would ultimately finish his career.
And the former Boro captain is confident Chris Wilder’s side can upset the odds this weekend and claim a play-off spot.
Boro travel to Deepdale to take on Preston North End knowing they must win and hope one of Luton Town or Sheffield United fail to win their respective matches.
The Hatters play host to Reading at Kenilworth Road and know a win will guarantee them a play-off spot after their scathing 7-0 defeat to Fulham on Monday swung the goal difference back in the favour of Boro should the two sides end level on points.
The Blades meanwhile host champions Fulham at Bramall Lane with Paul Heckingbottom’s side two points and two goals better off than Boro.
But Leadbitter believes there will be a twist this weekend and that Wilder’s side can force their way into the top six.
“I think they’re going to nick in there, I really do. I really hope they do it,” Leadbitter told The Mail.
“If you can nick into that sixth or fifth spot the momentum is then with you a little bit in the play-offs in the Championship.”
But should things not work out for Boro this weekend, Leadbitter believes success won’t be far away at the Riverside under Wilder.
“It’s absolutely brilliant the job he’s done.
“I’ve met him a few times. He’s a really good guy, I like him a lot. I think he’s brought something to Middlesbrough that they maybe haven’t had since Aitor [Karanka] was there and brought a connection and a togetherness between the players and fans and I love that.
“But whatever happens, I do think Chris will be a success at Middlesbrough and most importantly I believe he’s a good fella.”