10 memorable FA Cup matches and runs involving Boro

10 memorable FA Cup matches and runs involving Boro

Middlesbrough go into their FA Cup fourth round tie with Manchester City as the huge underdogs to come away from the Etihad Stadium with a result.

Boro beat League One side Barnsley in the third round to advance into the latest stage but there could not have been a harder fixture available to Aitor Karanka’s men than an away trip to the Premier League giants.

A win for Middlesbrough would almost certainly go down as one of the club’s greatest wins in the competition, especially as they are 14/1 with Betfair to win at City. Here are ten memorable FA Cup games and runs involving Boro:

1. FA Cup Final 1997 – Chelsea 2–0 Middlesbrough

Although the Boro lost the 1997 FA Cup final to Chelsea, it was a memorable occasion for the club as it was their first final in this competition which ensured a big day out at the old Wembley for everyone connected.

Chelsea got off to the perfect start as they took the lead after just 42 seconds, before doubling their lead with seven minutes left on the clock.

Sadly there was no trophy to show for it, but it was a Boro’s best year to date in the FA Cup.

2. Third Round, 1970 – Middlesbrough 2–1 West Ham

Back in 1970 West Ham were one of the best sides in England. Their team was full of England internationals so, when the Hammers travelled up to Ayresome Park, it was a big occasion in the north east.

Goals came from Derrick Downing and Hugh McIlmoyle as Boro recorded one of their biggest giant killings in the history of the club.

3. Third Round, 2011 – Burton 2–1 Middlesbrough

As an established Championship and former Premier League team, Boro often go into the third round of the FA Cup as one of the big boys who some of the lower league clubs want to play and beat to cause a shock of their own. Sadly that is exactly what happened in the 2010/11 season as Boro travelled to the Pirelli Stadium and were beaten 2-1 in front of just over 5,000 fans.

It all started well for Tony Mowbray’s men as they took the lead early in the second half, and they were still in front with ten minutes to go. However, the League Two club scored a couple of late goals to seal a famous win and send Boro packing.

4. 2006/07 FA Cup campaign

Many Middlesbrough fans felt 2007 was going to be their year in which their side were to win the FA Cup for the first time in their history. Unfortunately they eventually went out in the quarter-finals but Manchester United needed a replay at Old Trafford to eliminate Boro from the competition.

The campaign started in the third round where Boro beat Hull in a replay in a 4-3 thriller at Riverside. In the next round they were forced to a penalty shootout after extra-time of a replay against Bristol City, while in the fifth round, they got the better of West Brom on penalties to ride their luck once again.

Boro led Manchester United 2-1 for 20 minutes in the quarter-final until Cristiano Ronaldo equalised from the penalty spot at the Riverside. Another Ronaldo penalty in a replay at Old Trafford sadly brought Boro's cup run that year to an end.

5. 2001/02 FA Cup campaign

In 2002, Middlesbrough had a really good campaign in the world’s oldest competition which came to an end in the semi-finals where they were beaten narrowly 1-0 by eventual winners Arsenal, who were completing a double after also winning the Premier League.

The highlight of the run was a 2-0 victory over Manchester United at the Riverside in the fourth round, while they also defeated Blackburn and Everton on their run through to the last four.

6. Semi-final, 1997 – Middlesbrough 3-3 Chesterfield (AET)

Middlesbrough were involved in arguably one of the greatest semi-final ties in the history of the FA Cup in 1997 when they drew 3-3 after extra-time with Chesterfield at Old Trafford. The game eventually went to a replay, which was played at Hillsborough and, on that occasion, they advanced to the final courtesy of a comfortable 3-0 victory.

7. Third round, 2007 – Nuneaton 1-1 Middlesbrough

One of the most embarrassing moments in Middlesbrough’s history in the FA Cup came in 2007 when, as a Premier League side, Steve McClaren took his players to Conference North outfit Nuneaton. Boro were held to a 1-1 draw by the non-league side which is still described as one of the top 10 biggest FA Cup upsets in history in the competition. Fortunately, McClaren’s blushes were spared in the replay as they came out on top 5-2 to end Nuneaton’s run.

8. Third round, 1926 – Middlesbrough 5-1 Leeds United

Not many people, if any, will remember this result but, looking through the history books, this is one of Boro’s greatest moments in the FA Cup. At the time they were in the old Second Division, while Leeds travelled up to the north east as a top-flight side.

All the headlines went to Jim McClelland, and rightly so, as he scored all five of Middlesbrough’s goals against the First Division team to knock them out of the competition in spectacular style.

9. Third round, 1989 – Grimsby 2-1 Middlesbrough

Unfortunately this one is another giant killing that went against Middlesbrough. Boro were 13th in the First Division when they travelled down to play the Mariners who were positioned 20th in the Fourth Division. It should have been a one-sided affair with the visitors coming out on top, but it did not follow the script as the hosts sealed the victory courtesy of a 2-1 scoreline.

10. Fifth round, 1938 – York City 1-0 Middlesbrough

The older generation of Middlesbrough fans won’t want reminding about this particular fixture. Boro were heavy favourites to defeat the Third Division North side who had beaten Coventry and West Brom to reach the fifth round and set up this tie. Unfortunately, Middlesbrough were added to their victim list in York’s incredible run to the semi-final of the competition that year.

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