This season marks a decade since Chelsea and England captain John Terry truly began making his mark in the Chelsea first team. Sure, he broke through in the 1998/99 season but it was at the turn of the century where he began to look more at home and, after a spell at Nottingham Forest on loan, really started on the path to where he is today. He stands out as a beacon of success in Chelsea’s youth system, one which has been much derided over the last few years.

But what of his young counterparts from ten years ago? With a quiet period in the current youth and reserve world, let’s take the opportunity to look at the class of 1999/00 and see what they’re up to now. There’s been a mix of success and failure, and whilst nobody has hit the heights of Terry, there are definitely positives.

    RESERVES

STEPHEN BROAD
The young defender was released by Chelsea after a series of loan spells and settled in Essex at Southend United, one of the teams he had a temporary spell at. He then fell down the leagues and played at Kingstonian, Corinthian Casuals and Sutton United before retiring to become a taxi driver.

NEIL CLEMENT
Whilst Neil’s brother Paul has worked his way through the club’s coaching ranks to become one of Carlo Ancelotti’s valued staff, brother Neil has forged a strong football career largely spent at West Brom in The Championship and the Premier League. After a single Chelsea appearance and some loan spells, Neil has made over 300 outings for the Baggies and is still going strong, looking to contribute towards their latest promotion push, and at age 31, he still has it in him for another spell in the top flight.

NICK CRITTENDEN
After making a sensational debut in the 1997 League Cup, Nick’s Chelsea career didn’t really take off, as he made just one further appearance before departing the club. He spent four successful years at Yeovil Town in the football league before dropping down the levels to help Aldershot Town on their path back to league status. The next step was Weymouth where he played during their financial struggles, and he is currently at Dorchester Town.

WARREN CUMMINGS
After a loan spell at Bournemouth, Scottish-born Warren settled down on the south coast after his Chelsea release and has been there since 2003, with a few loan spells now and then. With nearly 200 appearances for the Cherries, he also has a single Scottish cap, achieved back in 2002.

SHAYNE DEMETRIOUS
Released by Chelsea early in the decade, he has had spells at non-league Hendon and Northwood, but his football career has gone quiet in recent years and he has since moved onto other ventures.

RHYS EVANS
A former England Under-21 goalkeeper, Rhys’ best career spell to date came at Swindon Town where he was impressive for a number of years. He then moved to Blackpool but failed to make a desired impact, moving to Bradford City on loan, before joining Millwall and then Bradford again permanently. Still a useful player at league level, he is the backup stopper at League One Bristol Rovers and aged 27 has recently signed a new contract to compete for the starting gloves.

MIKAEL FORSSELL
Were he not so ravaged by injuries, there is every chance Finnish international Forssell could still be at Chelsea scoring freely. As it is, he has suffered serious injuries to both knees and after a bright start to his career at both Stamford Bridge and in loan spells at Crystal Palace and Borussia Monchengladbach, he was eventually sold to Birmingham City. He fared well in the Premier League but further injuries saw the midland side cut their losses as he returned to Germany and Hannover, where he has done well. He will continue to score goals but is a shadow of the player he once was, and it continues to disappoint when you consider what he could have been if fate were kinder.

STEVEN HAMPSHIRE
Born in Edinburgh, when his Chelsea career came to an end Steven headed back north of the border and forged a career in the Scottish lower leagues. After spells at Dunfermline, Brechin (where he had his best times), and Stenhousmuir, he moved to Berwick Rangers in the third division. In the summer of this year he retired from football and went into the car valet business.

JON HARLEY
Breaking into the 1999 first team squad, Harley was a revelation along the left hand side, providing an energy and vigour few expected of the local youngster. He made 30 league appearances in five years at Stamford Bridge before moving on to Fulham, before loan spells at Sheffield United and West Ham. A permanent move to Bramall Lane saw a good run in the team but he then moved onto Burnley, where he had three great years and won their Player of the Year award for 2005/06. He joined Watford in 2008 and is a regular in their Championship team.

PAUL NICHOLLS
A well-travelled goalkeeper, Paul has turned out for a host of non-league sides including Fisher Athletic, Rushden & Diamonds, and Margate. Released by Sutton United in the summer due to an injury, Paul is perhaps best known currently as the individual who represents John Terry and handles his business ventures. A close friend of Terry and best man at his wedding, there has been growing controversy over John’s off-field activities in the latter part of 2009 and Paul’s name may become more prominent now than it ever was as a player.

SAM PARKIN
A big, strong striker who fared well at youth and reserve level for Chelsea, he never made it to the first team and instead has had a successful football league career. He has scored goals for Swindon, Ipswich and Luton, enjoying three prolific years at the former-most club, and after a loan spell at Leyton Orient last season is now at League One Walsall, where he has three goals so far this campaign.

LUCA PERCASSI
One of a few Italians signed by Gianluca Vialli, he made two substitute appearances at Stamford Bridge before returning to Italy at the turn of the century. Spells at Monza, Alzano and Spezia were disappointing, and in 2004 he retired from football to become a businessman.

JAY RICHARDSON
After signing with Exeter and making 18 appearances for the Grecians, Jay has done the non-league rounds, racking up time at Enfield, Crawley, Eastbourne, Croydon, Carshalton, Molesey, and Walton & Hersham. He has struggled to find success at any of them.

JOE SHEERIN
Joe made one solitary Chelsea appearance and since moving on is another who has done the non-league circuit. A brief period at Bournemouth was unsuccessful, and after playing for Kingstonian he helped AFC Wimbledon move up the league ladder with a prolific three seasons at the club. As the club moved up the ladder Joe struggled to keep up with their quality and left for Croydon Athletic. A second shot at the Dons was unsuccessful and he last played for Leatherhead.

DANNY SLATTER
Danny signed for Farnborough this summer and was a marquee signing for the club. He missed last season injured but before that had time at Welling, Chelmsford and Ebsfleet United outside the football league.

ROBERT WOLLEASTON
Highly considered by the coaches at Chelsea, Rob made one Chelsea appearance before embarking on what would be considered a disappointing career. He turned out briefly for Bradford and then Oxford United, but the majority of his career was played at Cambridge United, where he experienced relegation from the football league. He is attempting to return to that level now with Rushden and Diamonds in the Blue Square Premier.

    ACADEMY

DARREN BAXTER
One of the more well-travelled youngsters, upon departing Chelsea he moved up to Scotland to play for Hearts but a paperwork issue meant he was forced to play reserve football. He came back south to Worthing and then St. Albans City, but then headed across the Atlantic to play for the Toronto Lynx in the USA’s second tier. He had a successful spell in Canada and then moved into the Canadian League, staying in Ontario and playing for the Oakville Blue Devils. A year later he was back at the Lynx, and most recently had a short period back in England at Torquay.

LESLIE BYLE
One of a strong Scottish contingent under youth coach Jim Duffy, Leslie returned north at the end of his scholarship to play for East Fife. He has since moved on to local teams Armadale and Stoneyburn.

SAM DALLA BONA
Signed from Atalanta, Sam was one of Chelsea’s brighter prospects at the turn of the decade but with his first team opportunities apparently limited, he signed a Bosman free transfer with AC Milan. Unfortunately the return back home wasn’t a great success, as he was unable to break into Carlo Ancelotti’s Milan side. Loan spells at Bologna, Lecce and Sampdoria were equally uninspiring, so he dropped down a division to sign for Napoli. It was a clean break and he was enjoying his football in Serie B, helping the team return to the top flight. When they got there, it was the same story though, as he was sidelined in favour of better players. Needing regular football, he is spending this season out on loan in Greece at Iraklis.

GEZA HAJGATO
Geza has stayed in Wales for his entire post-Chelsea career, notching up appearances for Pontardawe Town, Pontypridd Town, and most recently Goytre United.

JOE KEENAN
Joe played twice for Chelsea and was on the fringes of the first team for some time, as he was farmed out to satellite side Westerlo and often impressed. Unfortunately, he broke his leg in 2002 and was never quite the same, falling down the leagues to Brentford and then Eastbourne Borough. To his credit, he has bounced back strongly and recovered his career abroad. He contributed well to Eredivisie team Willem II and then headed down under to play for Melbourne Victory in Australia. As he began to impress, Hibernian brought him back to the UK for a season in the SPL, but he was released last summer. He has recently signed a deal to play in the Australian league again next season for the new South Melbourne team.

LEON KNIGHT
A hot-shot since his early teens, Leon never lived up to his promise and whilst he had a successful league career, his personality has often rubbed people up the wrong way and he will have to work hard to get things back on the right path. He was loaned out by Chelsea around various teams and excelled at Huddersfield, but the Terriers chose not to make the deal permanent. Their loss wasn’t QPR or Sheffield Wednesday’s gain, but it was Brighton’s, who took him full-time after 4 goals in 2 league games and reaped the benefits. Leon scored 30 goals in 106 league games and ensured Chelsea would earn a £50,000 transfer fee when he scored the goal to seal promotion to The Championship. But this was the beginning of the problems for Knight, who fell out with Mark McGhee and moved to Swansea. He scored a debut hat-trick for the Swans and generally scored well, but again moved on. He became slightly nomadic, playing for MK Dons and then Rushden & Diamonds, with whom he had a contractual dispute which precluded him from playing in England until the deal expired. He stayed active and moved to Greece to play for Thrasivoulos Fila but flopped and has returned to British shores this season to play for SPL side Hamilton Academical. Still only 27, there’s time yet to return to his previous heights, but only if he wants to.

COURTNEY PITT
Courtney hit the headlines as a seventeen year-old when it was reported that the likes of Barcelona were interested in acquiring his prodigious talent, but perhaps it went to his head somewhat, because four years at Cambridge United’s Abbey Stadium isn’t a comparable career highlight. When Graham Rix took charge at Portsmouth in 2001 he took Pitt with him for £200,000 but he flattered to deceive and was loaned to Luton and then Coventry. Pompey cut their losses on him in 2004 and sold him to Oxford United on a free, where he would once again be under Rix’s tutelage. He lasted less than half a season before being released, and after a season at Boston he signed for Cambridge, where he has been ever since (despite being released in 2008, he was re-signed by the new manager the same summer).

ANDY ROSS
Born down south to Scottish parents, when he left Chelsea he moved to Scotland to play for Partick Thistle.

PAUL THORNTON
His post-Chelsea career has been scattered in the lower non-league at Bishop’s Stortford and Molesey.

Mark Hook, John Rattray, John King, and Mark Royal failed to stay in notable football at the end of their scholarships.

It’s an interesting mix, and one which hasn’t really changed ten years later. Players who depart Chelsea are still finding they can have an active career in the upper ends of the football league like Neil Clement and like Jon Harley, whilst others fall lower down the ladder like Jordan Tabor and Billy Joe King this summer. What is known is that Chelsea continue to help their old players find a move in the short-term, and have given them a solid footballing education with which to build upon. With over 70 players plying their trade in England and Europe who have come through the club, they’re doing something right, and they’ve been getting progressively better.

What will the next generation bring? Maybe we’ll have to see in 2019…