Ipswich Town and Arsenal are set to face each other in the Carabao Cup, with the match scheduled for 8pm BST at Portman Road. This encounter represents Arsenal's latest chance to win a major domestic trophy under manager Mikel Arteta, who has yet to lift any major cup during his time in charge. For Ipswich, the match is an opportunity to continue their history of facing one of England’s top teams, with the two clubs having met six times in league matches over the past 30 years, all of which ended in losses for Ipswich. Despite their league struggles against Arsenal, Ipswich has had some success in cup competitions. In November 2000, they secured a memorable 2-1 victory over Arsenal in the third round of the League Cup at Highbury. A decade later, the two teams met again in the semi-finals of the same competition. Ipswich took the first leg at Portman Road with a 1-0 win, thanks to a goal from Tamas Priskin. However, Arsenal won the second leg 3-0 at the Emirates, advancing to the final where they eventually lost to Birmingham City. In the current season, Arsenal reached the Carabao Cup final but fell to Manchester City, with Manchester City’s Nico O’Reilly scoring both goals in the match. This result highlights the ongoing challenge Arsenal faces in domestic cup competitions, despite their strong league performances. For Ipswich, the match against Arsenal is not only a test of their current form but also a chance to rewrite their history in one of England’s most prestigious cup competitions.