FA Cup History and Its Most Famous Upsets

The FA Cup is the oldest football competition in the world, and it's the one tournament where the impossible genuinely happens on a Saturday afternoon in February. A non-league club with a part-time keeper knocks out a top-flight side, and suddenly the whole country knows the ground's name. Here's how the competition got here, who's won it most, and the upsets that made its reputation.

Where it started

The first FA Cup final was played on 16 March 1872 at the Kennington Oval in London, and Wanderers beat Royal Engineers 1–0. That's the beginning of organised club football's oldest trophy — a competition that had been running for barely a decade before the Football League even existed.

Wanderers were an amateur side of Old Etonians and public school men. Royal Engineers were a military team. Neither would recognise the tournament that now takes in more than seven hundred clubs.

The record winners

There's a second record nobody at these clubs wants. Manchester United and Chelsea are joint for the most finals lost in FA Cup history, on nine each — United's ninth came before Chelsea's did, and the 2026 final put Chelsea level with them.

The upsets the competition is famous for

This is the bit people argue about down the pub, and there's no shortage of candidates.

What makes the Hereford and Sutton games land is that neither club was in the Football League at all. That's the FA Cup's whole selling point — the further down the pyramid you are, the more attractive the draw becomes, because there is a week when beating a top-flight club is genuinely possible.

Where the final has been played

The final has had four spiritual homes, and the gap between them is longer than most people expect.

One correction worth making, because it gets repeated constantly: Highbury was never an FA Cup final venue. Arsenal's own records show it hosting twelve semi-finals from 1929 onwards, which is a different thing entirely. Wembley's 1923 arrival didn't follow Crystal Palace directly either — there's a gap, and the final spent those years elsewhere.

How it works now

• 747 clubs were accepted into the 2025–26 competition — the entry count changes each season, so don't assume it holds.
• Replays have not vanished completely: they've gone from the main competition after the qualifying stage, so drawn ties there now go to extra time and penalties.
• The winners' payment for 2026–27 is £2,120,000. That's the payment for winning the final, not the total a club earns across the whole run.

The money is worth being precise about, because "the FA Cup winners get £2.1m" sounds like a season's haul and isn't. It's the final's payment on its own.

Going to a cup tie

Cup ties are a great day out for a group, especially the lower-league ones where the whole ground is close to the pitch. Availability depends entirely on the draw and what's released, so we can't promise anything until it's confirmed. Have a look at our football hub for what we arrange, or send us your group size and who you'd like to see through our contact page. And if you want the practical side of booking a weekend sorted, our stag FAQs cover the questions people ask us most.

All tickets, accommodation and activities are subject to availability and confirmation in your written quote. We don't arrange flights.