Monday night will see Chelsea enter the 2009/10 FA Youth Cup at the Third Round stage, and signals the start of another year of dreaming that the academy can go one better than they did two years ago, when they reached the Final only to be beaten by Manchester City.

That generation, under manager Paul Clement, featured one of Chelsea’s most productive groups of players in history, recent or not. From that group, Miroslav Stoch, Gael Kakuta, Jeffrey Bruma and Michael Woods have all featured for the first team whilst the likes of Rhys Taylor, Tom Taiwo, Patrick van Aanholt, and captain Nana Ofori-Twumasi are currently on loan at football league teams. It’ll be hard for second-year manager Dermot Drummy to repeat not only the feats of that class of players, but the quality of progression to the first team, yet there is room for optimism.

Last year’s team was a young one without much competition experience, and they were chucked in at the deep end with a third round clash at Old Trafford against a very talented Manchester United team featuring Federico Macheda and Daniel Welbeck. A great performance saw a 3-2 win on the night was followed by a 5-1 demolition of Walsall courtesy of Kakuta and Fabio Borini running riot, but their journey was to end prematurely with defeat against Liverpool at Anfield on a night where they flattered to deceive entirely. It meant the end of the Youth Cup road for some, but in turn it means that this year, the dreams are handed over to others.

The draw for Chelsea has been potentially kind, with an away trip to Charlton. The Blues have met the Addicks twice in the 2009 calendar year, running out 3-1 and 3-0 winners, but both games were at Cobham against younger line-ups. Monday’s fixture will be played at The Valley in front of what is expected to be a decent crowd, and playing on the big stage for the first time will be revealing for a number of the players likely to be involved. But just who are they?

Aldi Haxhia is likely to keep goal in this round at least, but when he has recovered from his foot injury Sam Walker is the incumbent number one and has been one of Chelsea’s best performers this season. He can win a game single-handedly and if the club are to go deep into the Cup, he will be a big part of that, especially with potential problems in defence. The regular Under-18 defensive partnership this season has been Danny Mills and Kenny Strickland, but Strickland is too old to play, with the competition rules stating players born before September 1st 1991 are ineligible. Rohan Ince is still injured and not expected back until the new year, whilst Nathaniel Chalobah is, rather interestingly, too young. He doesn’t turn 15 until December, and so falls outside of the youngest age allowance, which is to be born before September 1st 1994.

It offers Drummy a conundrum to solve, one which he is likely to attempt to solve by using Tom Hayden alongside Mills, with Ben Sampayo at right-back and Billy Knott likely at left-back. Jeffrey Bruma is still eligible but having played in two competitions already and being involved with the first team on a regular basis, it would surely be against his best interests to use him. Knott could face competition for the left-back berth from Aziz Deen-Conteh, but Drummy has shown faith with Knott ahead of him this season so far and will likely continue in that manner.

In midfield, we could conceivably see Conor Clifford drop back down from the Reserves to captain the team, as he is still eligible and spoke earlier this season of his desire to really do well in the competition. It could mean that regular defensive anchor George Saville takes a back seat, although he has played well more often than not and would still merit consideration. Ahead of them in midfield, Kaby and Josh McEachran should be pencilled in to play, with Anton Rodgers and Billy Clifford offering cover and versatility from the bench, with Clifford more likely to start if it comes to it. When fit, James Ashton could be a very useful player to have against tougher opposition, as his use of the ball is often impressive and belies his age.

To win the Youth Cup, a team needs to really score goals, and the potential firepower available to the club is plentiful. Gokhan Tore and Jacopo Sala are both reserve squad regulars who are young enough to play, but only Gokhan is expected to, with Sala having clearly graduated from the youth team setup. That offers the chance for Milan Lalkovic to play on the opposite wing (as Drummy has shown faith with a 4-5-1 of late as opposed to the club’s preferred 4-4-2 diamond) and Bobby Devyne to offer a change of pace with his dynamic running. Marko Mitrovic should spearhead the attack as the team’s top goalscorer this season, and Philipp Prosenik will be expected to chip in here and there as he has done in the league.

It’s a long and arduous road to the Final in May and the usual suspects of Arsenal, Man Utd, Man City and Aston Villa will be tough to beat if the draw brings the Blues together with them along the way, but for now, going into tomorrow night at The Valley, there’s every reason to dream.