TOMORROW afternoon, Jonathan Woodgate will make his managerial FA Cup debut when Middlesbrough host Tottenham. Given the quality of the opposition, his side could be in for a tough afternoon. Whatever happens, though, the experience will surely be more enjoyable than his first taste of FA cup action as a player.

“It wasn’t good,” said Woodgate, as he let his mind wander back to a January afternoon in 1999. “I was an 18-year-old, playing in the FA Cup for the first time with Leeds. We were playing against Rushden and Diamonds, it was my first match, and I got sent off.

“I rattled someone. I remember it was away at their ground, and I was devastated. We ended up drawing 0-0, but thankfully we won the game in the replay so I was pleased about that.”

The FA Cup was never particularly kind to Woodgate – he was also part of the Leeds team that was memorably humbled at Ninian Park when they were top of the Premier League and Cardiff were in the third tier – but his memories of other cup competitions are more enjoyable. Particularly when it comes to his time with tomorrow’s opponents, Spurs.

Woodgate won his only piece of major silverware when his extra-time header enabled Tottenham to see off Chelsea at Wembley in the League Cup final in 2008. Actually, ‘header’ is probably stretching things a bit. In reality, the decisive strike flew into Petr Cech’s net off his nose.

“Jermaine Jenas was lining one up, and I just thought I’d get a run on (Didier) Drogba,” said the Boro boss. “I was brave, stuck my head in there, and it went in, lucky really. It was the best goal I’ve ever scored with my nose.

“It was fantastic as a young player. As a kid, you always dream about playing in cup finals, so it was a dream come true really.

“All my family were there, and I thought we deserved to win it on the day to be honest with you. We had a really good starting XI who could beat any team on the day. I can’t remember the celebrations mind, it’s all a bit of a blur.”

Given his time at Leeds, Newcastle and Real Madrid, not to mention his eight international caps with England, it seems incredible that Woodgate only lifted one trophy in the whole of his playing career.

He admits his lack of silverware is regrettable, and concedes it acts as a compelling counter-argument to those who would argue he played in some truly ‘great’ teams.

“That trophy with Tottenham was the only thing I won, which is obviously something you look back on with a bit of regret, especially with the teams I played in,” he said.

““We had that spell at Leeds, and we also had a good team at Newcastle, but you can’t say a team is great unless you win trophies.

“You have to win trophies. People might say, ‘Well, you had a great team there’. But did we? Not really. You have to be winning trophies. You can’t do anything about it now.”

Equally remarkably, that 2008 success is also the last time Tottenham tasted any success, although they came within touching distance of one of the greatest moments in their history last summer when they fell at the final hurdle in the Champions League, losing to Liverpool in the final in Madrid.

Woodgate feels Mauricio Pochettino did a fantastic job as Spurs boss, and expects Jose Mourinho to build on the Argentinian’s ground work. He is still a firm favourite of the Tottenham support – he was greeted like a returning hero when he visited the new White Hart Lane for the first time at the end of last season – and would love to see his former club re-establish themselves as genuine contenders at the very top of the English game.

“I thought they would have won something under Pochettino,” he said. “I thought he did an amazing job there, and to get them to a Champions League final was absolutely unbelievable, especially with the budget he had.

“He hardly spent any money there, so he did an incredible job. I’m sure that’s on the horizon now with Jose Mourinho because he’s a serial winner.”

Middlesbrough’s FA Cup pedigree is largely based around their appearance in the final in 1997, when Roberto di Matteo’s first-minute strike for Chelsea briefly earned them an unwanted place in the record books, but Woodgate’s playing responsibilities meant he was not at Wembley to see his boyhood team contest the final.

He was at the national stadium in 1990 though, with his father and uncle, watching Colin Todd’s Boro side lose to Chelsea in the final of the Zenith Data Systems Cup.

“I remember that to this day,” said Woodgate. “We got beat 1-0, from a Tony Dorigo free-kick, and I was absolutely gutted.

“The biggest thing I remember was Tony Mowbray walking the team out in his blue blazer and grey pants. I remember the team – Owen McGee played as well, if I remember rightly – but that free-kick Dorigo put in was brilliant. I was devastated going back home.

“My dad and uncle drove us down from Teesside, and it felt like the longest drive ever going all the way down to London - mind you, it felt even further coming home after we’d got beat.”