The original Littlewoods League Cup trophy 1986-1990 that was presented to the winning teams

The original Littlewoods League Cup trophy 1986-1990 that was presented to the winning teams

A Victorian parcel-gilt silver Cup and cover, by Thomas Bradbury and Sons, London 1895, on spreading, with scrolling acanthus foliage, the domed centre with acanthus and palm leaves, with vase-shaped stem, the finial formed as a footballer, the body inscribed THE LITTLEWOODS CHALLENGE CUP, with circular plinth applied with silver-gilt plaque inscribed with previous winners - 1987 ARSENAL, 1988 LUTON TOWN, 1989 NOTTINGHAM FOREST, 1990 NOTTINGHAM FOREST, the trophy 27.5in. (70cm) high, with plinth 34in. (87cm) high, 127oz, 3,957grms, in blue felt lined wooden case with brass plaque inscribed THE LITTLEWOODS CHALLENGE CUP

The Littlewoods Challenge Cup was a prestigious English football cup competition sponsored by Littlewoods, a major UK retail company that was part of the larger Shop Direct Group. The brand’s involvement in English football helped raise the profile of the competition. It ran from 1986 to 1990. The tournament was also known as the Littlewoods Cup before sponsorship changed to Rumbelows in 1990 and later to Coca-Cola. It was regarded as a major domestic trophy, second only to the FA Cup, and allowed both top clubs and smaller teams to compete for silverware.

In the 1987 Final – Arsenal defeated Liverpool 2-1 with two late goals from Charlie Nicholas. In the 1988 Final – Luton Town shocked Arsenal 3-2, with a last-minute goal by Brian Stein, denying Arsenal back-to-back wins. In the 1989 Final – Nottingham Forest won 3-1 against Luton Town, thanks to goals from Nigel Clough and Neil Webb. In the 1990 Final – Nottingham Forest retained the trophy, beating Oldham Athletic 1-0, with Nigel Jemson scoring the only goal.

The tournament ceased to exist after the 1991-1992 season due to restructuring in English football. The format was replaced by the Football League Cup, which is now known as the Carabao Cup or the League Cup. Littlewoods' sponsorship boosted the tournament’s profile, and its branding became synonymous with the competition. When the sponsorship ended in 1990, the tournament was rebranded as the Rumbelows Cup before evolving into what is now known as the Carabao Cup (League Cup). The Littlewoods Challenge Cup remains a memorable chapter in English football history, especially for the clubs and fans who witnessed thrilling matches during its four-year sponsorship.

The cup was not made specifically for the Littlewoods Challenge Cup but repurposed from The Viscountess Furness Cup. The solid silver cup was made in 1895 and was given to the winning team in the company's football knockout tournament from 1920 until 1968. Then was later adopted by Littlewoods.

After the shipyard closed, the trophy was given to a school and later sold to a jeweller. When Littlewoods first sponsored the League Cup in 1987, they refurbished the trophy and displayed it in their Stockton store, and it became associated with the national competition.