Gareth Southgate is targeting success in this season's Carling Cup, starting with a win over Manchester United at Old Trafford tonight.
The Middlesbrough manager lifted the trophy back in 2004 when he skippered the club to their only major domestic honour.
Since then Boro have gone beyond round three twice in four attempts, going as far as the quarter-finals in 2005/06.
Southgate believes a run to the final is a possibility this season and pinpoints Portsmouth's progression to May's FA Cup final as the inspiration.
Pompey overcame Manchester United at Old Trafford on the way to Wembley and the Boro boss believes all successful cup runs include a tie against one of the 'big boys'.
He also points to his club's excellent record against the European champions in recent seasons.
"We have had some very good results at Old Trafford and some good performances and that would be the mindset again,'' he said.
"We don't fear going into any game, the confidence is still in the team to play, we know we are a threat on the break, we know we are a threat going forward and the shape of the team away from home.
"We've got to play as we did at Sunderland on Saturday and be prepared to keep the ball and attack Manchester United.''
Despite three defeats in their last four Premier League games, Southgate will not rest key players for tonight's tie with a view to keeping them fresh for Saturday's home game against West Brom.
He said: "It's an important competition, it's one we want to win.
"We've been given the toughest possible draw. It's a great draw for us as a club in terms of the profile of the game and the finance involved in it, but we now have to go there and try to beat them.
"The fact is you have to beat at least one of the big boys on the way to winning a cup competition,'' he added.
"Even Portsmouth, who maybe had good draws last year, had to beat United away to get to the final.
"If you look, most cup finalists have to win one big game on the way through.
"That's the challenge for us and in cup football anything can happen on the night.''
Whatever the outcome of tonight's match, Southgate recognises the huge gulf between his club and the champions.
The Reds can pull in more than 75,000 fans for every home match and their earnings from virtually guaranteed top-three Premier League finishes and continual European football puts them in a different financial league.
He said: "We go there tonight and one home game for them just in terms of ticket sales and size of crowd is something like three for us and that's what you've got to compete against.
"It's very difficult but that's the challenge we face.''