Charlton fans will have nightmares about the last time they played Ipswich as the two clubs meet again in pre-season.

Pre-season friendlies are often used as warm-ups, but the upcoming match between Charlton Athletic and Ipswich Town has a significant undertone. Both teams are facing unique challenges ahead of the upcoming season.

Ipswich Town’s owners are exploring a £350 million takeover, which could add to the club’s uncertainty. They’ve also had transfer setbacks, with one attempt to sign a 2025 Gold Cup winner falling through.

While Charlton Athletic’s Nathan Jones is busy creating Luton 2.0 through summer signings, their busy transfer business continues.

Given their opposing circumstances, the friendly, scheduled for Tuesday, July 29th at Colchester United’s stadium, becomes even more intriguing, especially since their last League One meeting two years ago ended so dramatically – and Charlton fans will not want a repeat of that nightmare.

Charlton’s quest for vengeance after their 6-0 Ipswich thrashing

In April 2023, Ipswich Town dominated Charlton Athletic 6-0 to move up to second place in League One.

Conor Chaplin scored a hat-trick, and substitute Freddie Ladapo added a quick brace. Charlton’s misery continued with a denied penalty appeal and a late red card for defender Ryan Inniss before Leif Davis scored in stoppage time.

Ipswich finished second that season under Kieran McKenna, who is still in charge at Portman Road. That season, they earned automatic promotion to the Championship.

McKenna has since led them to consecutive promotions, eventually reaching the Premier League. Meanwhile, Dean Holden led Charlton Athletic to a mid-table finish.

Holden was later fired, and Nathan Jones arrived at The Valley in February 2024, leading Charlton to Championship promotion through the play-offs. Their very different performances continued into the 2024/25 season, adding fuel to Charlton’s desire for vengeance.

While Ipswich struggled in the Premier League, winning only four games and scoring 36 goals on the way to relegation, Charlton won 25 league games and scored 67 goals in League One on their way to promotion.

This significant difference, with Charlton gaining momentum while Ipswich struggled in the top flight, fuels Charlton’s desire to prove they can now compete with a team that once humiliated them. It begs the question:

how will their upcoming pre-season friendly play out? One of the Championship’s newly promoted teams faces one of the Premier League’s recently relegated teams.

Charlton & Ipswich’s different journeys but same ambition

Aside from the historical grudge, this match is an intriguing look at two clubs approaching the Championship with vastly different recent experiences.

Ipswich have just returned from the Premier League, where they faced top-tier opposition on a weekly basis before being relegated.

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