A rare official programme for the 1909 FA Cup final between Manchester United and Bristol City carries a valuation of £15,000-20,000 ($24,054-32,072) to Graham Budd Auctions' November 4 sale in London.
The penny match card features the line up of the teams along with player listings and information such as height and weight.
The match was the first time that Manchester United had ever appeared in an FA Cup final, and was the first of their record 11 wins to date.
Earlier this year the earliest known FA Cup final programme, from 1882, made £30,000 ($48,108) - a 20% increase on its high estimate of £25,000 ($40,090).
Alex Stepney's 1977 Manchester United FA Cup final winner's medal is valued at £7,000-10,000 ($11,249-16,070).
The 9k gold medal is inscribed "THE FOOTBALL ASSOCIATION, CHALLENGE CUP, WINNERS, ALEX STEPNEY", and comes in a presentation case along with a photograph of Stepney receiving it.
The match saw Liverpool defeated by United 2-1, a result that denied Liverpool a treble after winning both the League and the European Cup.
Cyril Knowles' Tottenham Hotspur medal from Spurs' 1967 FA Cup final win over Chelsea is estimated at £7,000-9,000 ($11,249-14,463).
The final was the first to be played by two teams from London, leading the press to dub it "The Cockney Cup Final".
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