It’s an early Carabao Cup trip to League Two Bromley to kick off Town’s cup exploits and test the depth of the squad. Last season the Blues fell at their first hurdle with an on-penalties defeat to AFC Wimbledon in round two.

Their participation in this competition starts earlier this season as they enter in round one against a Bromley side who enjoyed a taste of league football for the first time in their history and finished the season in an impressive 11th place in League Two last season.

They are managed by Andy Woodman, who was head of goalkeeping at Arsenal before joining the Lilywhites in 2021. Not only has he got them promoted and kept them in League Two, he also lifted the FA Trophy with them in 2022 and is one of the most highly thought of managers in the lower tiers.

They started the league season with a goalless draw with Shrewsbury and followed it up with a 2-0 victory over Barnet, Town keeper Cieran Slicker making his debut for the opposition side in that one.

Goalkeepers

Grant Smith has been at Bromley for two seasons now having spent most of his prior career in the National League. The 31-year-old played 47 matches last season, keeping 16 clean sheets.

His back-up is 22-year-old Scotsman Sam Long who was limited to one league, three EFL Trophy and one Carabao Cup appearance last season. He conceded 10 goals across those appearances.

Dillion Addai, formerly of Chesham who has signed recently following a successful trial, is likely to be third choice.

Defenders

Bromley have a core of experienced defenders that are supplemented with some youth. The key feature across the backline is versatility which allows Woodman to play either a back three or a back four depending on the situation.

The most familiar will be former Arsenal defender Carl Jenkinson. The 33-year-old has 93 Premier League appearances and is no doubt a coup for that level but his fitness and injury record has always been an issue and he only made 13 appearances last season.

By contrast, 38-year-old Byron Webster is as consistent as they come. The experienced campaigner has made 560 career appearances across all levels of the EFL and the centre-back chalked-up another 30 last season.

There’s also a former Town youngster in the Bromley ranks. Omar Sowunmi spent time in the Town academy without ever making a first team appearance. He’s carved out a career, largely in League Two with the likes of Colchester, Sutton, Yeovil and now Bromley bringing a 6ft 5in tall aerial presence to their backline which saw him score five headed goals in the league last year.

That experience is complemented by the youthful exuberance of Deji Elewere, who swapped Charlton for Bromley on a permanent deal after two successful loan spells. He’s now made 41 appearances for the Lilywhites and was used across the backline last season.

Bromley have also added to the centre-half unit with the addition of Kyle Cameron, who spent last season at St Johnstone and then Barrow in two separate loan spells away from Notts County.

County is where he has played the majority of his football but as they’ve strengthened their squad, he’s a player that had become surplus to requirements and will be looking to prove his worth with a fresh start.

All of Bromleys full-backs/wing-backs were loanees last season, apart from Idris Odutayo and Brooklyn Ilunga. Odutayo largely played as a left centre-back towards the end of the season but featured as a left-back and a left wing-back with his versatility a useful attribute, seeing him start 32 matches, whilst Ilunga was largely used off the bench with just four starts.

Midfield

There’s quite a lot of turnover in the lower leagues so Jude Arthurs is definitely a rare case. The 23-year-old has been with Bromley since 2020 and has chalked up 174 appearances for the club. He spent the majority of last season forming a double pivot with Ashley Charles, who provided more of the cover that allowed Arthurs to get forward and find the net four times.

To compete with those two in the coming season, Bromley have raided Northampton for William Hondermarck, a former Norwich City academy player on a free transfer. A signing that will be seen as a coup given the majority of his experience has come playing at League One level.

They have also loaned in Ben Krauhaus from Brentford for the second time, having initially sold him to the Bees’ B Team back in 2024. He’s made 58 appearances in his time at Bromley scoring eight goals.

Ahead of that pair was Ben Thompson who started the season on loan from Stevenage but made the switch permanent in January. He finished the season with six goals and is another in this squad that has the majority of his experience at a higher level than League Two with 164 appearances in League One and 76 in the Championship.

Also joining the Lilywhites from Northampton is Mitchell Pinnock. The 30-year-old versatile attacker largely played on the wing in League One last season, making 45 starts scoring two goals and assisting seven and returns to the club where he made one appearance way back in 2014 and will provided valuable experience and cover, filling in as a left wing-back in the first two matches

Forwards

Without doubt Bromley’s stand-out player last season was Michael Cheek. The 33-year-old found no problem making the step up into League Two, exceeding his 23-goal haul in the National League the season before with a wonderful 25 to go alongside his seven assists.

That form saw him named in the League Two Team of the Season and he’ll be hoping to reach the 20s again this season, having already got off the mark against Barnet with a Conor Chaplin-esque finish from a clever free-kick.

Woodman was very versatile, sometimes playing Cheek up front on his own but at other times looking to partner him with Nicke Kabamba, who joined halfway through the season from Barnet, where he had scored 10 goals in the National League.

He only got off the mark from Bromley with a goal in each of his last two games but will be hoping to fire some more in with a full pre-season under his belt. Like Cheek, he also found the net right at the death against his former club on Saturday.

Behind them in the pecking order are Marcus Dinanga and Marcus Ifill, neither of whom saw much game time last season. However, Dinanga scored five goals in pre-season, four of which came against Tottenham U21s in a very exciting 5-2 victory and earnt him a start in the first game of the season against Shrewsbury.

Ifill on the other hand looks to have been converted to a right wing-back for the first couple of games of the season.

The final player to mention is Corey Whitely. The 34-year-old is another versatile player but enjoys his football the most when he’s playing just off the main striker in a Chaplin type role. He loves a cup competition with two goals and three assists in three FA Cup games last season.

The Teams

As is the case with the early-stage cup competitions it’s highly likely Kieran McKenna will make wholesale changes as his counterpart Woodman is also likely to do, based on his team from last year's first round where they lost to AFC Wimbledon, who then beat the Blues in the next round.

With injuries hitting, Elkan Baggott, Cameron Humphreys and Fin Barbrook are likely to get another chance to make a claim for a squad place, whilst the re-signed Jens Cajuste is likely to get minutes in some capacity but how many is up in the air.

Prediction

Bromley have a good record in cup competitions and have made a good start to the season. With a home crowd they’ll be fired up for this one. If Town make the wholesale changes most are anticipating it could be a close game. I’m going for a 1-0 away victory.

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