Arsenal host Crewe Alexandra in the fifth round of the FA Youth Cup on Monday and to mark the occasion we looked at the last time the two sides met - the 1999/2000 Under-17 play-off final.

It was pitched as the battle between talented youngsters Jeremie Aliadiere and Dean Ashton and it was the Gunners striker who triumphed, helping his side to a 4-3 aggregate victory over the Railywaymen with a second-leg brace.

Both youngsters went on to feature for their respective first teams, and this is what happened to the other players involved.

Arsenal

Craig Holloway

Then: Schoolboy Craig had featured in the majority of Arsenal’s Under-17s games that season and was an England Under-16 international. The goalkeeper started in both legs of the 1999/2000 play-off final.

Now: Craig left Arsenal for Farnborough in 2004, spending the second half of the 2004/05 season on loan with Southend. The goalkeeper also had spells at Ebbsfleet, Bromley and Margate before ending his career at Dartford. He is now a coach at Danson Sports Under-15s.

Israel Da Silva Filho

Then: Spotted by Gunners scouts while playing for Brazil in France. An attacking right back in the Cafu mould. The defender completed both legs of the 1999/2000 play-off final.

Now: Israel was the first Brazilian on Arsenal’s books - ahead of Edu - and helped the Gunners win the FA Youth Cup in 2000, but the defender left the club soon after having failed to make an impact.

Ben Chorley

Then: A first-year scholar who scored a hat-trick of penalties in Arsenal’s 7-0 win against Crystal Palace earlier in the season. The defender completed both legs of the 1999/2000 play-off final.

Now: Ben left Arsenal to join Wimbledon in 2003 with eight months left on his Gunners contract, and remained with the side after they relocated to Milton Keynes. From there he had spells at Gillingham, Tranmere Rovers, Leyton Orient and Stevenage. The defender is now a regular for Portsmouth in League Two.

Then: Highams Park schoolboy who featured in Arsenal’s victorious FA Youth Cup side. The defender completed both legs of the 1999/2000 play-off final.

Now: Ryan won the FA Youth Cup the following season and signed a professional contract at Arsenal that summer. He made his first-team debut in 2002 and earned his first senior start against Southampton - the first match of the 49-unbeaten streak - before joining Bournemouth. The defender featured 77 times for the Cherries but retired due to injury and went into coaching. Ryan is now under-13s coach at Arsenal.

Moritz Volz

Then: A first-year scholar who was also a Germany Under-15 international. He had just been given a European first-team squad number. The defender was an unused substitute in the 1999/2000 play-off final.

Now: Moritz played twice for Arsenal before joining Fulham where he featured over 100 times and scored the 15,000th Premier League goal. The defender then returned to his native Germany for a brief spell with FC St. Pauli before moving to current club 1860 Munchen.

Niccolo Galli

Then: An Italy Under-16 and Under-17 centre half who provided the Gunners with a towering presence at the back. The defender completed both legs of the 1999/2000 play-off final.

Now: Niccolo won the Youth Cup in 2000 before returning to Italy on loan with Bologna to finish his studies. The defender featured in Serie A and Italy’s youth teams before tragically dying in a road traffic accident aged 17. Bologna named their training centre after him and retired his No 27 shirt. Arsenal observed a minute's silence upon the news of his death. Arsene Wenger said: “I have no doubt in my mind that had he lived, he would have been captain of Arsenal and of Italy.”

Alex Bailey

Then: Highams Park schoolboy who had featured at full back for Arsenal Under-19s that season. An England Under-16 international, the defender was an unused substitute in the 1990/2000 play-off final.

Now: Alex won the Youth Cup in 2001 but was released soon after and signed by Chesterfield. He spent three seasons at Saltergate, scoring one goal, before a short spell at Halifax Town and two seasons at St Albans City, where he was released.

Jermaine Pennant

Then: Became Arsenal’s youngest ever first-team player when he featured against Middlesbrough in the Worthington Cup aged 16 years 319 days. The forward was an unused substitute in both legs of the 1999/2000 play-off final.

Now: Jermaine was a regular for England Under-21s and played 26 times for Arsenal, winning the Community Shield, and had short loans at Watford, Leeds United and Birmingham before joining the Blues permanently. The forward then switched to Liverpool where he won the Community Shield again and played in the Champions League final defeat against AC Milan. After that, Jermaine had short spells at Portsmouth, Real Zagaroza, and Stoke City before joining the Potters permanently. More recently he has featured for Wolverhampton Wanderers on loan and is currently playing for WIgan Athletic after a short spell with Indian Super League club FC Pune City. Jermaine’s youngest debutant record has since been surpassed by Cesc Fabregas and Jack Wilshere.

Stephen Santry

Then: Had suffered badly from injury that season but bounced back to full fitness and earned himself a place on the bench for the FA Youth Cup final. Stephen was a 74th-minute substitute in the second leg of the 1999/2000 play-off final.

Now: Stephen was released by Arsenal in 2002 and played non-league football but has drifted out of the game.

Rohan Ricketts

Then: Played in every round of Arsenal’s FA Youth Cup success. He also featured for the Gunners reserves that season. The midfielder completed both legs of the 1999/2000 play-off final.

Now: Rohan made one appearance for Arsenal, in the League Cup against Manchester United, before becoming only the fourth player to move from the Gunners to Tottenham Hotspur, in 2002. He then spent time at Coventry City and Wolverhampton Wanderers on loan before making the latter move permanent. Another loan followed, this time to Queens Park Rangers, and he then spent a season at Barnsley and Toronto. Rohan’s search for regular first-team action took him to Hugary’s Diosgyori VTK, Moldova’s Dacia Chisinau, Germany’s SV Wilhelmshaven and Shamrock Rovers. The midfielder then returned to England for a month with Exeter City before he moved to India’s Dempo, Ecuador’s Deportivo Quevedo and Thailand’s PTT Rayong. Rohan is currently playing for Eastern Sports Club in the Hong Kong Premier League.

Steve Sidwell

Then: One of the stars of the FA Youth Cup team, scoring in both rounds of the final. Had been with the club since the age of 12. The midfielder completed both legs of the 1999/2000 play-off final.

Now: After successful loan spells at Brentford and Brighton & Hove Albion and winning the FA Youth Cup in 2000 and 2001, Steven left Arsenal in 2003 to sign for Reading. The midfielder spent four seasons with the Royals, playing more than 180 games and featuring for England Under-21s, before signing for Chelsea. After a year at Chelsea, Steve moved on again, this time to Aston Villa where he was a runner-up in the 2010 League Cup, and then played four seasons with Fulham. The midfielder is now a first-team squad member at Stoke City.

Jermaine Brown

Then: South London schoolboy who was a product of the Arsenal academy system. Can play in midfield or attack. The midfielder completed both legs of the 1999/2000 play-off final.

Now: Jermaine left Arsenal in 2003 and spent a season at Colchester United before joining Boston United briefly. The midfielder then played non-league football for Lewes, Margate and Aldershot Town. Jermaine last featured for Chelmsford City.

John Spicer

Then: Highams Park schoolboy of immense promise who had represented England at under-14, under-15 and under-16 levels. The midfielder was a 76th-minute substitute in the second leg of the 1999/2000 play-off final.

Now: John played one League Cup game for Arsenal, a substitute appearance against Rotherham United, before joining Bournemouth in 2004 after a successful loan spell. The midfielder played for Burnley for three seasons and then joined Doncaster Rovers. From there, John joined Leyton Orient on loan before signing for Notts County. He last played for Southend United in 2013, where he was released.

Nicky Nicolau

Then: Another Highams Park schoolboy who had appeared for the Gunners Under-19s that season. The midfielder was an unused substitute in the 1999/2000 play-off final.

Now: Nicky left Arsenal in 2004 to join Southend United permanently after a successful loan spell with the Shrimpers. The midfielder helped Southend win the League Two play-off in 2005 and then had short spells at Swindon Town and Hereford United. Nicky moved to Barnet where he spent three seasons before short non-league spells with Woking, Dover Athletic, Boreham Wood, Lincoln City, Chelmsford City and Welling United. The midfielder is currently unattached having been released by Chelmsford after a second spell with the Essex club.

Then: A young French striker of great promise who was at France’s famed Clarefontaine Football Academy prior to joining the Gunners. The forward completed both ties and scored twice in the second leg of the 1999/2000 play-off final.

Now: Jeremie played 28 times for Arsenal’s first team, scoring five times, and helped Arsene Wenger’s side win the Premier League, Community Shield and finish runners-up in the League Cup. He joined Middlesbrough in 2007 after loan spells at Celtic, West Ham United and Wolverhampton Wanderers as well as regular action for France Under-21s. The forward then returned to France to play for Lorient having featured 86 times for Boro and scored 12 goals. Jeremie had more success in his native country, netting 31 times in 83 appearances. He is currently playing for Umm-Salal SC in Qatar.

Jerome Thomas

Then: Was with Luton Town until the previous summer. Possesses great pace and an eye for goal. Another veteran of the FA Youth Cup campaign. Jerome started both ties and scored in the second led of the 1999 play-off final.

Now: Jerome played three times for Arsenal’s first team after winning the FA Youth Cup in 2000 and 2001, and had two loan spells with Queens Park Rangers before joining Charlton Athletic permanently in 2004. The forward played more than 100 times for the Addicks then moved to Portsmouth after a short loan spell with the south-coast club. Jerome joined West Bromwich Albion in 2009 and featured more than 100 times for the Baggies before spending a season on loan with Leeds United. He is currently playing for Crystal Palace.

Carlin ItongaThen: A prolific striker who scored twice in the Gunners’ semi-final win against West Ham United. The forward started both ties and scored in the second leg of the 1999/2000 play-off final.

Now: Carlin won the FA Youth Cup in 2001 and played one first-team appearance, as a substitute against Manchester United in the League Cup, and joined Sheffield Wednesday on loan in 2002. The forward was released upon his return and had brief spells with Enfield, Cmabridge City, Kettering Town and, most recently, Fisher Athletic.

Then: The youngest member of the Gunners’ squad, David was a Highams Park schoolboy and England Under-15 international. The forward was a 94th-minute substitute in the second leg of the 1999/2000 play-off final.

Now: David played nine times for the first team and scored once, against Middlesbrough in the FA Cup. After successful loans to Norwich City and Blackburn Rovers, the forward joined Rovers permanently in 2006 and played over 100 times for the Premier League side before joining Tottenham Hotspur in 2008. He won goal of the month in October 2008 for his long-range strike against Arsenal and Spurs finished League Cup runners-up in the same season. David struggled for playing time and had short loan spells with Birmingham City, West Ham United, FC Rostov and Blackburn Rovers. He retired from football in 2014 aged 29, having won seven caps for England, and is now a co-owner of a restaurant in Spain.

Crewe Alexandra team

Nick WilsonThen: Nick was the club’s regular under-17 goalkeeper and had played in all their matches that season. He had kept seven clean sheets during that campaign.

Now: Nick currently plays amateur football for non-league Canning Town.

Adam Yates

Then: Could operate on either side but was most comfortable at right back. Possesses great pace and loves to get forward.

Now: Adam did not feature for the first team and played non-league football with Halifax Town, Leek Town, Morecambe and Burton Albion before securing a move back into the Football League with Port Vale in 2009, where he is currently a regular.

Lee Bell

Then: Lee’s tough-tackling approach and ability to attack saw him become an important part of the under-17 side.

Now: Lee made over 50 appearances for the first team, scoring three goals, before he moved to Burton Albion after loan spells at Shrewsbury Town and the Brewers. He then joined Mansfield Town, Macclesfield Town and Crewe Alexandra again before re-signing for Burton in 2012, for whom he currently plays.

Tom Betts

Then: A defender who was on the scoresheet on four occasions that season. Was involved in the Youth Cup squad.

Now: Tom went on loan to Icelandic outfit Iprottabandalag Vestmannaeyja in 2003 and was unable to feature for the first team upon his return due to international regulations. He quit football in 2005 and is now an engineer.

Alex Morris

Then: Could play anywhere across the back four but had formed a good understanding with Betts in the centre of defence.

Now: Alex was rewarded with a first-team squad number in 2006 after battling through injuries that had kept him out for two seasons. The defender was forced into early retirement and is currently Crewe Alexandra Under-18s coach.

Neil Coverley

Then: Had improved considerably that season and was looking to push for a first-team place the following season.

Now: Neil played non-league football but has drifted out of the game.

Ben Rix

Then: A midfield general who impressed with his composure, trickery on the ball and his superb range of passing. Dario Gradi gave him the number 33 in the first-team squad.

Now: Ben made over 100 first-team appearances in eight seasons with Crewe Alexandra, and had success on loan with Scarborough and AFC Bournemouth, before he was released in 2009. He retired from football the following year having last played for South West Peninsula League side St. Blazey AFC.

Carl Frost

Then: A midfielder with an eye for goal. Could also play in a more advanced position - never afraid to shoot as he scored 14 times for the under-17s.

Now: Carl had two loan spells at Witton Albion before joining Leek Town in 2004. He broke his leg that season and retired from football in October 2007 due to injury problems. Carl the came out of retirement soon after to play for Leek once more, but was released in January 2008.

Ian Jeffs

Then: Another goalscoring midfielder who could become a star of the future. He had already scored 16 goals for the under-17s, including four against Birmingham City.

Now: Ian impressed on loan at Iprottabandalag Vestmannaeyja (IBV) in 2003 and signed a permanent deal the following season. After two years with the Icelandic side, the midfielder moved to Swedish side Orebro for a season before re-joining IBV in 2007. Short spells at Fylkir and Valur then followed but the moves did not work out and Ian is now in his third spell at IBV.

Michael Higdon

Then: The first-year scholar impressed that season and would be a fundamental part of the under-17 side next year.

Now: Michael played 81 times in four seasons for the first team, scoring 10 goals, and secured a move to Falkirk in 2007. After impressing for the Bairns, the forward joined Scottish Premiership side St Mirren and then Motherwell, where he averaged a goal every other game. Michael joined Eredvisie side N.E.C. in 2013 before returning to England the following year with Sheffield United, for whom he currently plays.

Paul Edwards

Then: The club had high hopes for the under-17 striker who had scored 17 goals that season. He was expected to progress into a first-team prospect.

Now: Paul made 12 first-team appearances for Crewe Alexandra and also had loan spells with Stafford Rangers and Southport. He has since drifted out of the game.

Dean Ashton

Then: At only 16, Dean had a huge potential to go a long way in the game. Big, strong and brave, he was built like an old-fashioned centre forward but was blessed with a delicate touch.

Now: Dean played more than 150 games for the first team, scoring 74 goals before becoming Norwich City’s record signing at £3m. The forward netted 18 times in his debut season and moved to West Ham United. His goalscoring form at the Hammers impressed Fabio Capello and he was rewarded with an England cap, against Trinidad & Tobago. Dean retired aged 26 through an injury suffered in an England training session.

David Vaughan

Then: Young David was a tricky and creative winger who possessed fine close control and balance. An under-17 regular who scored seven times that season.

Now: David played more than 200 first-team games before moving to Real Sociedad for a year. He then joined Blackpool and played more than 100 games for the Seasiders, including a season in the Premier League. David then spent three seasons at Sunderland before he was loaned to Nottingham Forest, for whom he currently plays. The forward has played 38 times for Wales.

Lee Westwood

Then: Found it difficult to displace Ashton and Edwards from the forward line. A hardworking forward with an eye for goal.

Now: Lee was forced into early retirement after breaking his leg. He has since played a huge part in helping his younger brother, Ashley, make the step up from League One football with Crewe Alexandra to becoming a Premier League regular with Aston Villa.

James Wilcox

Then: A promising forward who had been on the fringe of the under-17 side. Forced his way into contention with a brace against Bolton Wanderers.

Now: James has drifted out of the game.