Luton, Boro and Boreham Wood look to cause FA Cup 5th-round upsets

Chelsea’s first visit to Luton since 1991, minnows Boreham Wood look to pull off one of the biggest shocks of ALL TIME at Everton and Boro eye another upset after dumping out Man United… things to look out for in the FA Cup fifth round this week

  • Seven of the eight 2021-22 FA Cup fifth-round ties take place Tuesday-Thursday
  • Peterborough, Stoke, Middlesbrough, Luton and Boreham Wood seek shocks
  • Southampton vs West Ham and Liverpool vs Norwich are top-flight clashes 

The hectic football season continues this midweek with the return of the FA Cup at the fifth-round stage.

After the dramas and giantkillings that occurred in the fourth round there are just 16 teams left.

With seven of the eight ties taking place across Tuesday, Wednesday and Thursday (Nottingham Forest vs Huddersfield is on Monday night) – Sportsmail previews those midweek fixtures.



These sides have only met once in the FA Cup and that also happened to be in the fifth-round back in 1981 with Manchester City triumphing courtesy of a Tommy Booth goal.

That victory helped City reach the FA Cup final where they lost to Tottenham. Fast-forward 41 years now though and success is part of City’s DNA.

Pep Guardiola’s side sit top of the Premier League and are all-but through to the Champions League quarter-finals – barring an epic capitulation against Sporting Lisbon.

This is in stark contrast to Peterborough who have just re-appointed Grant McCann as manager but sit bottom of the Championship – eight points from safety – having taken just one point from their last six matches.

Peterborough be warned, City have won each of their last 11 FA Cup matches against sides from a lower division, netting 40 goals along the way. 

Giantkilling rating: 1/5

Manchester City go in as firm favourites for their FA Cup fifth-round match at Peterborough

This was a regular Premier League fixture just a few years ago until Stoke City were relegated at the end of the 2017-18 campaign.

Prior to their drop to the Championship, the Potters had endured a miserable record against Palace – winning just once from their previous 10 encounters in all competitions, losing eight and drawing the other.

Looking at the form of both teams, a win for Palace should be the likely outcome once more. Stoke are winless in their last four matches (losing the last two). Palace have won just once in their previous four games but did so impressively in dismantling Watford.

Oh and in Michael Olise they have a player who is lighting up the FA Cup at the moment. The 20-year-old has scored and assisted in his last two FA Cup matches, with no player in this season’s competition having a direct hand in more goals than the Crystal Palace winger so far (four).

Giantkilling rating: 2/5

Michael Olise has a direct hand in four FA Cup goals this season – more than any other player


Middlesbrough were one of the giantkilling stories in the FA Cup fourth-round when they won away at Manchester United on penalties. Their reward? A fifth-round tie at home to Premier League opposition – this time in Tottenham.

The Riverside Stadium has sold out, for the first time since 2017, with fans hoping to see the Championship side produce another upset.

That could happen depending on what Spurs turns up on Teesside. Their last three matches have seen impressive wins at City and Leeds sandwich a horrible defeat at Burnley.

Middlesbrough have only won one of their last 13 meetings with Tottenham in all competitions (drawing four, losing eight). To make it more daunting, Tottenham have never lost to Middlesbrough in the FA Cup – winning four and drawing twice.

You just never know under the lights on Tuesday night though…

Giantkilling rating: 3/5

Middlesbrough players celebrate after winning at Manchester United in the fourth round



Chelsea have to bounce back from their heart-breaking Carabao Cup final defeat on penalties to Liverpool on Sunday with a trip to Luton Town in the FA Cup.

It won’t be an easy fixture for the Club World Cup and European champions with Luton building momentum in the Championship at present. The Hatters had a brilliant February, winning five out of six games in the Championship, and are now up in the play-off places after beating Derby on Saturday.

Luton and Chelsea are meeting in the FA Cup for the second consecutive season, with the Blues running out 3-1 winners in the fourth round at Stamford Bridge last term. Chelsea went on to reach the FA Cup final too.

Historically Kenilworth Road hasn’t been kind to the west London outfit, having won just one of their last five meetings there and losing the other four – although that most recent one was in December 1991.

Chelsea were last eliminated by lower league opposition this far into the competition in 2007-08, a 1-0 defeat by Championship Barnsley at Oakwell in the quarter-final, and it seems unlikely that history would repeat itself down to their squad depth.

Giantkilling rating: 2/5

Luton Town enjoyed a fine February – winning five of their six Championship games

Luton have won four of their last five home meetings vs Chelsea (pictured John Dreyer in 1991)


The first of two all Premier League ties is on the south coast as Southampton host West Ham United.

Both teams are fortunate to be in the fifth round after getting by Coventry City and Kidderminster respectively.

Southampton have only lost once at St Mary’s all season but West Ham have never lost to the Saints in the FA Cup, winning three and drawing three of their six meetings.

Remarkably, if Southampton advance it will be the first time since 1904-05 and 1905-06 that they have reached the FA Cup quarter-finals in consecutive campaigns.

Meanwhile, West Ham are trying to break their own hoodoo having gone winless in nine FA Cup away games against fellow Premier League sides (drawing three and losing six), though have progressed twice via replays.

Giantkilling rating: None as both are Premier League sides

Ralph Hasenhuttl’s Southampton haven’t made successive FA Cup quarter-finals in 116 years


The other all-Premier League affair sees Liverpool host Norwich. It is the second meeting in 12 days for the two teams, with Liverpool coming back from a goal down in the Premier League to win 3-1 on February 19.

Liverpool have already beaten Norwich three times in all competitions this season, twice in the Premier League and once in the League Cup – they’ve never beaten a team four times in a single season across league, FA Cup and League Cup.

All roads point to another Reds victory, who will be buoyed by their Carabao Cup final shootout win over Chelsea on Sunday.

Remarkably though, this is only the second time under Jurgen Klopp that the Anfield outfit have reached the FA Cup fifth-round (losing to Chelsea in 2019-20). The Merseysiders last reached the quarter-finals in 2014-15, before losing to Aston Villa in the semi-finals.

Giantkilling rating: None as both are Premier League sides 

Liverpool and Norwich will meet for the fourth time this term after being paired in the FA Cup



The final midweek FA Cup fixture is also on Merseyside as Premier League outfit Everton welcome National League side Boreham Wood.

This tie is truly David vs Goliath and represents the ‘magic’ of the FA Cup.

Boreham Wood stunned Championship high-flyers Bournemouth in round four and the magnitude of that win will be ten-fold if they could replicate that at Goodison Park in what will be their first-ever competitive meeting with a top-flight side.

It’s going to be a tough ask for Boreham Wood though, with Everton having progressed to the quarter-finals of the FA Cup on 11 of the last 13 occasions they’ve reached the fifth round, including each of the last five.

However, Toffees boss Frank Lampard will be aware of the goalscoring potential of the opposition. Of sides left in the competition, only Luton and Chelsea (seven each) have had more different goalscorers in this season’s FA Cup than Boreham Wood (six).

The question is will Boreham be able to capitalise on any chances they get?

Giantkilling rating: 1/5

Boreham Wood reached the FA Cup fifth round thanks to their brilliant win at Bournemouth

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