Chelsea’s 64th League Cup campaign begins with the visit of League Two side AFC Wimbledon, who will aim to make light of the 63-place gulf in respective league positions.

This 7.45pm kick-off is the Blues’ first round two tie since 23 August 2016, and our 100th League Cup match at Stamford Bridge, where we have a 64 per cent win rate from the previous 99.

Chelsea have the honour of being the capital’s first winners in 1964/65, and have brought the trophy to Stamford Bridge five times in total, though it has eluded the club since 2015 – the longest stretch since 1998. Mauricio Pochettino will hope to improve on last season’s exit at the first opportunity despite a changed and youthful starting XI.

There are one or two connections between tonight’s combatants. Johnnie Jackson was manager of our young loanee Mason Burstow at Charlton in 2022, while a predecessor, Mark Robinson, is the Blues’ Development Squad head coach. Chelsea’s early-1990s reserve team skipper Terry Skiverton is Jackson’s assistant. After the draw Skiv joked he’d been banned from mentioning his old club around the training ground.

Wimbledon arrived at this stage by beating Coventry 2-1 in round one at Plough Lane with two goals at the death.

The last lower division side to knock us out of the League Cup were Burnley in round four at Stamford Bridge in 2008 (after extra-time and penalties). Huddersfield, in 1999, were the last non-Premier League team to oust us after 90 minutes.

League Cup wins

9 Liverpool 2022 (most recent)
8 Manchester City 2021
6 Manchester Utd 2023
5 Chelsea 2015
5 Aston Villa 1996
4 Nottingham Forest 1990
4 Tottenham 2008

Team news

If Mauricio Pochettino drew up a wish list ahead of Friday’s hosting of Luton Town, it’s likely it included a brace for rejuvenated Raheem Sterling, a well-earned first goal for Nico Jackson, two assists for Malo Gusto (no Premier League player has created more), a clean sheet for Robert Sanchez, and three points in the bag.

He might also have preferred a league fixture next for continuity of momentum, but his approach to tonight’s tie has been made clear: ‘We are going to use four or five young guys from the Academy, 16- or 17-year-olds,’ he revealed. ‘It's because we need young guys to bring to the first team because we have some players who cannot play tomorrow.’

The youngest player on the bench against Luton was 19-year-old winger Diego Moreira. Highly-rated new shot-stopper Djordje Petrovic, meanwhile, will have to wait for his opening, Poch having confirmed Robert Sanchez will start tonight.

And while the injured rest up and Thiago Silva is possibly rested, squad members less involved up to now such as Marc Cucurella, Bashir Humphreys, Lesley Ugochukwu, Ian Maatsen, Noni Madueke, and Burstow (against his former coach), may be offered a chance to shine at some stage.

The Blues’ coaching staff will have noted how Forest Green Rovers pressured Wimbledon’s midfield into errors and their defence’s discomfort against quick passing and movement in and around the area.

On pre-season tour Chelsea won 5-0 against Wimbledon’s League Two rivals Wrexham, who recently played out a 1-1 draw at Plough Lane.

Scouting the opposition – Wimbledon

Wimbledon are a phoenix club, rising from the ashes of the old ‘Crazy Gang’ outfit, whose remnants moved to Bedfordshire to form MK Dons in 2003. Fans launched AFC Wimbledon and the new club climbed the football pyramid, though they were relegated back to their current League Two perch in 2022.

How seriously will the Dons take this competition when their overriding concern is a return to League One? Very: 'It’s not a day out,’ is head coach Jackson’s stance. He and his team will be battling for an upset and ‘right up for it’.

After a disappointing fall-away and dice with relegation last season, Jackson resolved his squad lacked experience and physicality. After plenty of ins and outs to make a more robust group, his focus turned to tightening the defence.

Despite the absence of preferred full-backs Huseyin Biler and Jack Currie and centre-back Paul Kalambayi’s recovery from knee surgery, he has been rewarded with three clean sheets in five league games. The Wombles currently sit fifth in the third tier of English football.

The former Spurs man will be concerned at losing captain Jake Reeves and fellow midfielder Armani Little to injury during Saturday’s draw. However, minutes after replacing his skipper, James Ball scored his first goal since signing, and Harry Pell played one half in place of Little.

Their main danger is probably dribbling right winger James Tilley, who’s accounted for four goals and an assist. Chelsea should also be wary of the Wombles’ set-plays, and they have height in their team. Four of their nine goals in all competitions have come from headers, most recently a well-worked corner on Saturday.

Prior to that first-half strike their earliest goal had come in the 54th minute. Instead, the Wombles have cleaned up towards the end of games with six goals arriving on or after the 80th minute. Late goals might especially be a factor in a competition with no extra-time in its early rounds. (That said, they conceded to Troy Deeney towards the end of Saturday’s draw.)

Despite the additional injuries at the weekend, the Wombles are likely to field the strongest possible squad and hope the Blues are off-colour on the night.

Carabao Cup round dates

Round 3 w/c 25 Sep 2023

Round 4 w/c 30 Oct 2023

Quarter-final w/c 18 Dec 2023

Semi-final (1st leg) w/c 8 January 2024

Semi-final (2nd leg) w/c 21 January 2024

Carabao Cup final Sun 25 Feb 2024

• NB All fixtures except the final may be moved for live TV.

League Cup – the history

This is the Blues’ first round two League Cup match since League One Bristol Rovers were the visitors in August 2016. Michy Batshuayi marked his first start by scoring twice in a 3-2 win.

This is only the second time Chelsea and Wimbledon have met in this competition. In round five of the 1998/99 edition, at Selhurst Park, then home of the Crazy Gang, Chelsea were big favourites.

Gianluca Vialli’s men were defending champions and had beaten Arsenal 5-0 in the previous round, contributing towards a 19-game unbeaten run. That sequence also included a 3-0 thrashing of the Wombles in the league, but it was the hosts who prevailed 2-1 against a much-changed Blues side. ‘We now have to see how we cope with defeat and it might be useful for everybody,’ reasoned the Blues’ player-manager.

The Blues have reached the final nine times, most recently 2022 and an unfortunate shoot-out loss to Liverpool, but were beaten 2-0 at Man City in round three last season.

This competition has been useful for handing minutes if not exactly debuts to young stars. Among the goalscoring debutants, though, were 17-year-old Peter Osgood (two) against Workington in December 1964 (2-0), Kurt Zouma with the opener at home to Bolton in September 2014, and Reece James at home to Grimsby in 2019 (7-1).

Significant Chelsea careers were also launched in this competition: John Terry against Aston Villa in 1998 (4-1), Branislav Ivanovic at Portsmouth in 2008 (4-0), Cesar Azpilicueta against Wolves in 2012 (6-0), as well as current squad members Ian Maatsen (vs Grimsby 2019, 7-1), and Thiago Silva and Ben Chilwell at home to Barnsley in 2020 (6-0).

Since their return to the Football League in 2011, Wimbledon have reached the third round of this competition only once, losing 3-0 at Arsenal in September 2021.

They will have a spring in their step after playing six games unbeaten in all competitions, and reached this stage with a stirring 2-1 comeback victory at home to Championship Coventry, thanks to Ryan McLean’s close-range winner.

Transfer window closure

Poch’s final squad for the campaign will be settled after the transfer window closes at 11pm on Friday. Here is everything else you need to know about deadline day.

Carabao Cup regulations

The draw for round three of the Carabao Cup will take place on tonight, at the end of the televised round two tie between Doncaster Rovers and Everton. The winner of this competition will earn a place in the Europa Conference League play-off round.

A clear result is required on the night in this competition, and up to the second leg of the semi-finals and the final itself that will be achieved without extra-time being played or replays. Instead, should the score be level after 90 minutes the match will be decided by penalties in the ABAB format.

Five substitutions (plus concussion replacements) are allowed.

Chelsea’s League Cup shoot-out record

2021/22 Final Liverpool L 10-11

2021/22 Round 4 Southampton W 4-3

2021/22 Round 3 Aston Villa W 4-3

2020/21 Round 4 Tottenham L 4-5

2018/19 Final Man City L 3-4

2018/19 Semi-final Tottenham W 4-2

2015/16 Round 4 Stoke L 4-5

2011/12 Round 3 Fulham W 4-3

2009/10 Quarter-final Blackburn L 3-4

2008/09 Round 4 Burnley L 4-5

1983/84 Round 2 Leicester W 4-3

By Rick Glanvill and Paul Dutton