A decade on from their last EFL Cup meeting, Cheltenham Town and Charlton Athletic will clash at EV Charger Points Stadium on Saturday.
The Robins prevailed back in 2016, but they now languish in League Two while their first round opponents are preparing for another season in the Championship.
Match preview
Cheltenham have finished 15th and 18th since dropping down to League Two in 2024, after a slow start damaged any hopes of promotion last season.
Aiming to regain their place in England's third tier, Steve Cotterill's side will soon kick off a new league campaign at home to Rotherham United, but first they must host Charlton in the cup.
Having lost five of their last six EFL Cup ties while conceding an average of more than three goals per game, it is fair to say the Robins have struggled to make an impact on this knockout competition.
But after several summer signings, the Gloucestershire club can now aim to reach round two, as competitive football returns to Whaddon Road this weekend.
Following a 2-0 defeat to MK Dons in their final pre-season friendly, Cheltenham will try to replicate the result of their first-round clash with Charlton 10 years ago - a 1-0 home win.
In league games, though, Charlton won both of the last two meetings, which took place during the 2023-24 campaign.
However, the London club have also lost their last three EFL Cup ties on the road, including last year's second round exit to Cambridge United.
The Addicks then went on to secure 19th place in the Championship standings, finishing six points above the drop zone.
Still under the management of Nathan Jones, they have been busy in the transfer market, intending to avoid another relegation battle and potentially contend for the playoffs.
After three wins, a draw with Maribor and a loss to Wimbledon, Charlton recently completed pre-season by losing 3-0 to Reading, but the real action begins this weekend.
Cheltenham Town pre-season form:
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Charlton Athletic pre-season form:
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Team News
Cheltenham could start several new boys on Saturday, with goalkeeper Wyll Stanway, midfielder Shaun McWilliams and central defender Pierce Sweeney all expected to play.
Former MK Dons winger Joe Tomlinson should also be involved, but new loan signing Kirsten Otchere - who scored three goals in four pre-season appearances for Leicester City - may start on the bench.
George Miller is favourite to lead the hosts' attack, following his haul of seven League Two goals last term.
Meanwhile, Charlton could name a strong XI for their last game before next week's Championship opener at home to Derby County.
Summer signings Ivan Mesik, Billy Koumetio, Danny McNamara and Millenic Alli should all be involved.
Karlan Grant - who came off the bench when these clubs met 10 years ago - recently returned to his boyhood club and could join Matt Godden in the final third; Scotland striker Lyndon Dykes has been released.
Cheltenham Town possible starting lineup:
Stanway; Tomkinson, Cundy, Sweeney, Nurse; Shipley, Stevenson, McWilliams, McCann, Tomlinson; Miller
Charlton Athletic possible starting lineup:
Kaminski; McNamara, Jones, Koumetio, Bell; Coventry, Docherty; Campbell, Knibbs, Grant; Godden
We say: Cheltenham Town 1-3 Charlton Athletic
While Cheltenham have home advantage for this EFL Cup tie, Charlton are a cut above their hosts in terms of quality.
The Championship side should stride through, leaving their League Two opponents to contemplate yet another early exit.
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