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Manchester United vs Tottenham: an FA Cup history

A look back through the past meetings of the semi-finalists.

Manchester United v Tottenham Hotspur - FA Cup 4th Round Photo by Alex Livesey/Getty Images

Saturday’s FA Cup semi-final between Manchester United and Tottenham Hotspur will be the 11th meeting of the two sides in this oldest competition of them all. Well, actually, it will be the 16th, what with replays and all. But it’s the 11th time they’ve been drawn together. Look, we didn’t mean to start this off in such confusing fashion. Let’s go again.

Saturday’s FA Cup semi-final between Manchester United and Tottenham Hotspur will not be the first meeting of the two sides in this oldest competition of them all. (Oh, we’re so clever) Here’s a look back at the history of this generally quite entertaining fixture.

1888-89, first round

Here, courtesy of Wikipedia, are some things that happened in January 1899. Spanish rule ended in Cuba. Rapid Vienna were founded. Queens and Staten Island were incorporated into New York City. The Southern Cross Expedition, precursor to the more famous journeys of Scott and Shackleton, crossed the Antarctic Circle. And in London, Newton Heath played an FA Cup tie against Tottenham Hotspur, the first meeting of two clubs that would go on to win the thing 20 times between them.

It was a 1-1 draw. Newton Heath’s goal was scored by Scotsman Joe Cassidy, one of the club’s earliest legends. He scored over 100 goals for the club over two spells, and stood as United’s record scorer until the great Sandy Turnbull came along. Sadly for the Heathens, the replay didn’t go as well. William Bryant scored a hat-trick, but Spurs scored five.

1922-23, second round

Come the early 20s, the Heathens had descended a couple of rungs down the moral ladder to become the Red Devils*, and Manchester United had begun the business of ups and downs. Before World War One they’d picked up two league titles either side of an FA Cup win; afterwards, they’d declined markedly, eventually getting relegated to the Second Division in 1921-22.

So when they drew 1921 FA Cup winners Spurs in the second round, they had a chance to indulge in a bit of giantkilling. This is not an opportunity often given to United sides: the downside of fame, success, and extremely strong branding is that you don’t often get to play the underdog. The magic of the cup always flows in the other direction. Unfortunately, they made a mess of this rare opportunity: Spurs won 4-0 at White Hart Lane.

* Actually, the Red Devils nickname wasn’t picked up until the sixties. But that would ruin a good line.

1925-26, second round

Third time lucky. United were a yo-yo club for much of the interwar period, but ‘25-26 was a season in the First Division. To celebrate this flourish of competence, United went on a bit of a cup run, dispatching Port Vale in the first round, then drawing Spurs in the second. A 2-2 draw at White Hart Lane took the tie back to Old Trafford, where unanswered goals from Charlie Rennox and Joe Spence sent United through.

Fun fact about Charlie Rennox: his name wasn’t short for “Charles”, as you might expect, but “Clatworthy”. Perhaps unsurprisingly, he appears to be the only Clatworthy of note as far as the internet is concerned; Wikipedia can only offer various appearances as a surname, a village in Somerset, and an associated reservoir. Apparently it means “homestead where burdock grows”. We can only offer our belated congratulations to his parents for their liberated imagination.

Anyway, United needed a replay to beat Sunderland in the third round, saw off Fulham in the fourth, and then made a mess of the semi-final, losing 3-0 to Manchester City at Brammall Lane. A sad end to the adventures of Clatworthy Rennox.

1961-62, semi-final

The only previous semi-final meeting between these two sides fell in the long shadow of the Munich air disaster. Though United’s league campaign ended with a disappointing 15th, their showing in the cup suggested that the rebuilding work was taking shape.

This was David Herd’s first season at Old Trafford after his move from Arsenal, and he scored United’s goal at Hillsborough. Cup holders Spurs, however, were a mighty fine side. This was the great team of Jimmy Greaves and Cliff Jones, and they both scored before half-time. United, helped by a convenient hailstorm, pulled one back near the end, but Spurs had time to add a third and reach their second final in as many years. They won that one too.

However, United made it to Wembley in 1963, where two goals from Herd and one from new signing Denis Law secured United’s first post-Munich trophy. The season after that a 17-year-old named George Best made his first team debut. And you know the rest.

1967-68, third round

Pfft, who cares? United had bigger cups to win …

… oh, fine. George Best and Bobby Charlton scored for United at Old Trafford, but a young Martin Chivers picked up two for Spurs and forced a replay. Four days later, down in London, United lost 1-0. By convenient coincidence, United’s next league fixture was Spurs (a), and this time United won. All three possible results — win, lose, and draw — in the space of a week. Fine, fine work all round.

1978-79, sixth round

Another Spurs-United cup tie, another replay. People really used to love cup football, didn’t they? Anyway, Spurs had Ozzie Ardiles and Ricki Villa in midfield, and it was the former that scored at White Hart Lane. But his goal was cancelled out by Mickey Thomas, so it was back up to Old Trafford once again. And up in Manchester, Spurs’ dreamy midfield was undone by a big header from a set piece and a poke through the keeper’s legs.

United made it all the way to Wembley again this season, only to find themselves on the wrong end of one of the great FA Cup sucker punches. Two-nil down against Arsenal with five minutes to go, goals from Gordon McQueen and Sammy McIlroy dragged United back to 2-2 and blew the whole game to pieces … until Alan Sunderland ran up the other end and ruined everything. Not worth the quiz question, in our humble one.

1979-80, third round

Back for more next year, and another replay just for good measure. This one went less well for Dave Sexton’s entertainers. They got the draw at White Hart Lane, but couldn’t take advantage back at Old Trafford. And let’s be clear, this wasn’t just “oh dear, Spurs are pretty good, we lost, what a shame.” By the time Ardiles clipped in the only goal of the game, in the 117th minute, noted outfield player Glenn Hoddle had been playing in goal for more than an hour.

Could have just sacked Sexton then and there and saved everybody a year.

1996-97, third round

Anyway, after another decade or so of mucking about and a couple of cup wins under Ron Atkinson, United entered the 90s and were good again. Here we find them in Eric Cantona’s final season, as defending league champions and cup holders, in pursuit of the the elusive Double Double. And Spurs, struggling with injuries and with two teenagers up front, didn’t put up too much resistance. Paul Scholes got the first, a neat poke home after a slick passing move, and then David Beckham did his freekick thing.

Their attempts to retain the trophy didn’t make it past the next round, however. After a 1-1 draw with Wimbledon at Old Trafford, United went down to Plough Lane for a proper mess of a cup tie, with more missed chances than really makes sense. The Londoners prevailed, though perhaps the most memorable moment of the game was a last minute overhead kick “equaliser” from Peter Schmeichel, which was ruled out by the jobsworth officials simply for being clearly and obviously offside. No sense of occasion, these linesmen. No flair for the dramatic.

2007-08, fourth round

What a time of glory and riches this was. Cristiano Ronaldo, Wayne Rooney, Carlos Tevez, and Louis Saha — who was brilliant, shut up — all in the squad together. All types of goals, from all types of angles. And most of them down to Ronaldo, who scored 42 in all competitions this season, including two against Spurs in the fourth round. Admittedly his first was a penalty, while his second — United’s third — was rather chucked in by goalkeeper Radek Cerny, but hey. It’s a numbers game. Just ask Harry Kane.

2008-09, fourth round

… and then United went and bought Dimitar Berbatov. More glory! More riches! And more FA Cup wins over Spurs. Roman Pavlyuchenko gave Tottenham an early lead, but a deflected Paul Scholes grass-trimmer drew United level after half an hour, and Berbatov’s inevitable winner followed just a minute later. In front of the visiting Spurs fans, he held his arms out wide and almost smiled. For anybody else it would be a muted celebration; for Berbatov, it was the equivalent of taking off his shirt and setting it on fire.

We miss him so much.