The dates for the group stages of the Checkatrade Trophy were confirmed on Tuesday morning.
The Addicks will face Southampton’s Under-21 side at The Valley on Tuesday 30 August. Crawley will make their first appearance at The Valley on Tuesday 4 October, and Russell Slade’s side travel to Colchester on Tuesday 8 November.
The top two in each section will qualify for a regionalised second round tie.
The Addicks suffered another ignominious cup exit at the hands of League Two newcomers, Cheltenham, on Tuesday evening.
A 17th minute stike from former Valley trainee, Harry Pell, was enough to send the Robins through to the next stage.
Worryingly, both Ricky Holmes – again Charlton’s best player – and Brandon Hanlan had to go off after sustaining injuries.
Holmes was withdrawn almost immediately as a precaution. He limped off with a foot injury, but Slade is hopeful he will be fit to face former club, Northampton, on Saturday.
Holmes’ effervescence and crossing ability have been shining lights in the Addicks’ disappointing start to the season.
Slade opted for a 4-4-3 formation at Whaddon Road, with Hanlon, Nicky Ajose and Ademola Lookman the three front runners.
Karlan Aheare-Grant was the only attacking option on the bench, Lee Novak was not involved. Roger Johnson was sent forward at the death, as the visitors tried to rescue the game.
Johnson was booed from the off by the travelling fans, but went close from a couple of corners.
Nicky Ajose had the ball in the net after five minutes, but was adjudged offside. He had Charlton’s best chance on the night, touching a Holmes left-wing cross agonisingly wide in the first half.
Once again, a set piece was the Addicks’ undoing. A long throw on the left from Daniel O’Shaunessy was not cleared properly, and when the ball was returned, Pell was able to apply the finishing touch.
Next up for Slade’s men are two Valley clashes in four days, Northampton are the visitors on Saturday, followed by Shrewsbury three days later.
Two good results are essential if the early malaise is to be nipped in the bud.
Charlton: Rudd, Foley, Konsa, Johnson, Fox; Holmes (Ahearne-Grant 68), Crofts, Jackson; Hanlan (Holmes-Dennis 80), Ajose, Lookman.
Subs (not used): Phillips, Thomas, Pearce, Solly, Muldoon.
Booked: Fox (foul), Crofts 90 (dissent), Johnson 90+4 (foul).
Cheltenham: Griffiths; Suliman, Parslow, O’Shaughnessy, Cranston (Jennings 90); Waters (Barthram 90), Pell, Whitehead, Holman; Wright, Morgan-Smith (Rowe 90).
Subs (not used): Kitscha, Lymn, Bower, Thomas.
Goal: Pell 17.
Booked: Holman 61 (time-wasting), Morgan-Smith 72 (foul), Jennings 90 (time-wasting).
Referee: Brendan Mallone (Wiltshire).