Middlesbrough boss Jonathan Woodgate is surprised by the lack trophies at former club Tottenham.
Woodgate hosts his former club on Sunday in the third round of the FA Cup.
He reflected: "I thought they would have won something under Mauricio Pochettino, I thought he did an amazing job, especially with the budget he had.
"But I'm sure that (silverware) is on the horizon now with Jose Mourinho, because he's a serial winner."
Woodgate was Tottenham's match-winner in the League Cup final against Chelsea in 2008 after a Dimitar Berbatov penalty had cancelled out Didier Drogba's first-half opener to force extra-time.