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Anderton: It's hilarious to see Sherwood in the dugout, but I always knew he'd be a boss

Darren Anderton currently has not one, but two reasons to feel a little nostalgic.

AFC Bournemouth, the fifth and final club he represented in an 18-year playing career, will host Liverpool on Saturday in an FA Cup tie that conjures up memories of his own David and Goliath battle with the Anfield club 22 years ago.

Meanwhile, a Tottenham side coached by three of his former White Hart Lane team-mates are playing with the same carefree swagger as Ossie Ardiles' 1994/95 'Famous Five' side, of which Anderton was a key component.

"Bournemouth have gone from strength to strength over the last three or four years and there is a lot of confidence in the city that the boys can do well on Saturday," Anderton tells FourFourTwo.

"The question is obviously how they stop Suarez, but that’s a question Premier League teams are asking every week and not many have been able to do it. We don’t know what team Brendan Rodgers will pick, but I’m sure the Bournemouth players would like Suarez to play so they can pit themselves against the very best, and that’s what the fans want too. Of course it’ll be really difficult, but you never know. Liverpool have conceded five in two games and I’m sure that’s something that Eddie Howe has looked at."

The sight of John Barnes - like Anderton, in Bournemouth for a charity event arranged by official FA Cup sponsors Beko - brings back frustrating memories for Anderton, the former Portsmouth, Tottenham and England star.

Anderton gave Portsmouth an unlikely extra-time lead in the 1992 FA Cup semi against Liverpool at Highbury, a strike which had looked like earning the Hampshire club a place in the final. Then Barnes hammered a 116th-minute free-kick against the post, gifting Ronnie Whelan a tap-in to take the game to a replay. Liverpool eventually scraped past a drained second-tier outfit on penalties.

"I wish it had been Golden Goal in extra time - his free-kick bloody killed us!", Anderton laughs. "But all my memories of that time are good. Just to be involved in that FA Cup run and to get into a semi-final with what would now be a Championship team - the team I started out with - was incredible. We were a really young team with a few very good senior players, and we certainly held our own against one of the best sides in the country.

"Those sort of games don’t come around very often, and that's why it's important that Bournemouth's players enjoy the match on Saturday. The main thing is to not be overawed - you have to believe you’re good enough to be on the same pitch as those big names.

"But that’s the way Bournemouth have gone about things over the past few years; they’ve been on the up constantly, so they may be used to being underdogs by now."

Another team seemingly on the up are Spurs, for whom Anderton, despite the 'Sicknote' tag, played 364 times between 1992 and 2004 - a period which he is at pains to point out saw him suffer FA Cup semi-final heartache on a further four occasions.

In the third of those four defeats - a 2-0 extra-time loss to an Alan Shearer-inspired Newcastle United - Anderton lined up alongside not only Tottenham's new manager Tim Sherwood, but also coaches Les Ferdinand and Steffen Freund.

"It’s hilarious to see the three of them sat there on the bench," Anderton jokes. "They’re great guys, which is the main thing for me. Players respond to great people, and they’ve been there and done it. They know what the club's all about. I’m sure they’ll work well together.

"You can already see that the team is more positive. It seems to me that they're really going out to win games, whereas before it was a case of setting out to not get beat and if they could nick a goal, then so be it. To me, that’s not the Tottenham way.

"Villas-Boas and Spurs did great last year, and even when he went the team weren’t in a bad position, but they were winning games 1-0 and it wasn’t great to watch, if I’m honest."

Anderton's career

Portsmouth 1990-92 - 77 (13)

Tottenham 1999-04 -364 (51)

Birmingham 2004-05 -24 (3)

Wolves 2005-06 -26 (2)

Bournemouth 2006-08 -72 (9)

Sherwood seemingly agreed, and in his first Premier League match in charge - a trip to Southampton - he picked two strikers in front of a midfield crammed with attacking players. The result was a open and compelling 3-2 victory, achieved entirely differently from the cautious and sometimes overly patient style preached by Villas-Boas.

Before the ink had even dried on the teamsheet at St. Mary's, comparisons were being made to Ossie Ardiles' infamous '5-0-5' formation featuring an attacking quintet of Anderton, Nick Barmby, Ilie Dumitrescu, Teddy Sheringham and Jürgen Klinsmann. Yet Anderton doesn't believe the current Spurs team will be caught out quite as spectacularly as the 1994/95 vintage, and suggests Sherwood has the tactical know-how to prepare Spurs for whatever tests may lie ahead.

"I’d like to think they can defend better as a team!" he laughs, when asked to compare the vintages. "If you’re going to be attack-minded, you’ve also got to work on the defensive side - I’m sure they're doing that. Back then, if an attacking player asked what our defensive responsibilities were when we lost the ball, Ossie would say: 'Well you’re all good players, you shouldn’t lose the ball' - that was as far as our defensive training went.

"It was an exciting team and good fun to play in, but we were never going to win anything. Tim is knowledgeable enough to be aware that while there are certain games when you’ve got to go out and be attacking to break down defensive teams, there are others where you’ve got to be more aware of the opposition."

Sherwood has long been highly regarded by the Spurs hierarchy, but his appointment as Villas-Boas' replacement last month still caught many outside the club by surprise. Foreign coaches including Frank de Boer, Louis van Gaal, Michael Laudrup and Mauricio Pochettino were all linked with the post before Tottenham opted for the seemingly less glamorous former Blackburn midfielder.

Despite the raising of eyebrows among the Twitterati, Anderton insists he always knew Sherwood would find his way to the dugout.

"As a player he was a leader. He had his views and he didn’t hold back. We had lots of meetings with Glenn Hoddle and Tim was always pretty vocal about where we were going right and wrong - he wasn’t just saying things for effect, when he spoke he did it with belief. 

I think it will come down to Spurs and Liverpool for that fourth spot"

"He was a thinker, but he also knows that at times it's not rocket science. Tottenham have got good players and I think the way he sees it is that he’s giving them the opportunity to play to the best of their ability - he’s taken the shackles off a bit.

"They’ve got a great chance. What Spurs have going for them is that the squad is very strong. As we get towards the end of the season, when injuries start stacking up, that will become a very important factor. I think it will come down to Spurs and Liverpool for that fourth spot."

For this weekend at least, both Liverpool and Anderton's eyes will be fixed firmly on Bournemouth.

Darren Anderton was speaking at the launch of Official FA Cup Supporter Beko’s Keepy-Uppy Challenge. To enter, visit – Beko will donate £1 per entry to Barnardo’s.