Jonathan Woodgate is convinced it is a matter of when rather than if Jose Mourinho wins Tottenham Hotspur some silverware.

It was Woodgate’s header that won Spurs their last major trophy, 12 years ago in the League Cup Final. Now the manager at his hometown club, Middlesbrough, Woodgate will take on Mourinho for the first time in the FA Cup on Sunday with nothing but admiration for the Portuguese.

“[Mauricio] Pochettino was an incredible manager and Mourinho was the only one who could really have come in above him,” said Woodgate, who has recovered from a poor start to his first season with four wins on the spin over Christmas.

“He’s another incredible manager, a serial winner. If you’re going to sack Pochettino, you replace him with another world-class manager in Mourinho. I’m sure he’ll win a trophy at Tottenham.”

Woodgate was the surprise choice to replace Tony Pulis at Boro in the summer, but chairman Steve Gibson was willing to invest in one of the club’s own. And when others might have panicked as Boro slipped into the bottom three back in the autumn, Gibson remained calm.

“I’m miles and miles away from where those two are,” added Woodgate. “I’m six months into my journey and you have to take it step by step. I don’t know where it will end, if you can get through season after season, that’s the most important thing.