Championship side Middlesbrough have made a respectable three signings in the transfer window so far.

It sounds less glamorous when you point out two of these additions are goalkeepers - but they are much-needed after the depletion of this department in the last year or so and Neil Warnock will look to add a few more players to his squad before the start of the 2020/21 campaign.

With pre-season already underway and the next campaign starting in just over a month, these further signings could come in very quickly - but our focus in this piece is on the past. We're turning back the clocks to list ten players the club struggled against over the years.

Thankfully for Warnock's side, none are likely to come up against them next season. Can you guess any of the ten?

When you have, click through this gallery and see if you managed to get any!

Along with Dennis Bergkamp, Henry is probably the best player Arsenal have ever had.

He was sublime at Highbury and the Emirates, playing a key part in the 2003/04 'Invincibles' season before leaving the club for FC Barcelona in 2007.

The Frenchman scored 228 goals for the Gunners in two separate spells - and 13 of these came against Middlesbrough - who must have dreaded playing against the forward in his peak.

Not only did they have to watch out for Henry - but the likes of Robert Piers, Freddie Ljungberg and Bergkamp too. What a nightmare for Boro.

In his 16 appearances against the Teesside club, he also picked up six assists to add to his seven goals. You could criticise Middlesbrough's defence - but the Frenchman was unstoppable in the early noughties.

Alan Shearer is Alan Shearer, there's no surprise he scored so many goals, but he was particularly prolific against Middlesbrough.

The two faced each other 20 times - with the Geordie and former England international grabbing himself 11 goals. Put it this way, they wouldn't have wanted to play him every week.

Shearer scored 374 goals in his playing career at a domestic and international level, being a key part of the memorable Euro 96 campaign and playing most notably for Blackburn Rovers and boyhood club Newcastle United, remarkably winning a Premier League title with the former.

He now appears regularly as a pundit on the BBC.

Between 2005 and 2007, the Nigerian was actually a Middlesbrough player!

He joined from Portsmouth in 2005 before going on to Everton two years later and when he was in England around that time, he was a goalscoring machine.

Unlike Henry, Yakubu didn't manage to record any assists against Boro but did score an impressive nine goals in just eight games.

A rate of over a goal per game - an unbelievable record! And a pain in the backside for Middlesbrough.

Although the Yak had declined when he returned to England with Reading in 2015, it's his time at Everton, Middlesbrough and Portsmouth that will be remembered the most - and he can take great pride in making over 50 appearances for his country.

Let's just not talk about THAT miss at the 2010 World Cup.

The Dutch magician was mentioned earlier - and after seeing Thierry Henry make the list - it's no surprise to see Bergkamp get in on the act either.

His eight goals and three assists against the now-Championship side is an impressive total but this is no fluke, because he's replicated that sort of record against many other teams too.

While the Invincibles team inevitably helped him to reach that impressive 11 goal contributions total, they wouldn't have been able to do it without him and the Dutchman was ever-present in the team that went on that impressive 49-game unbeaten run.

And although he was a thorn in Middlesbrough's side, at least he didn't do this magical turn and finish against them as he did against Newcastle United.

To this day, it's one of the finest goals that's ever been scored in the Premier League.

Liverpool legend Robbie Fowler is best known for his time at the Merseyside club - but he also spent time at Leeds United and Manchester City - so Middlesbrough just couldn't get rid of him.

He recorded eight goals in 17 games against the Teesside outfit, a tidy return for a man who was consistently firing on all cylinders for Liverpool.

Where is he now? Managing out in India at East Bengal - and he started his coaching career out in Thailand when he finished his playing career in 2012.

It's certainly an interesting path to take but it's refreshing to see him do well abroad and could potentially return to England to further his managerial career one day.

He may be content in Asia for the time being, but keep an eye on this one.

It's surprising to see the Ivorian only play against Middlesbrough eight times after spending such a long time at Chelsea - but he still did more than enough damage and they can only be thankful he didn't get more opportunities at the Riverside or Stamford Bridge to inflict further pain.

Considering it took Fowler 17 matches to score eight goals, Drogba bagging six in eight appearances is a very impressive total and just goes to show how much of an asset he was to the Blues.

He will be remembered for his equaliser and winning penalty against Bayern Munich in the 2012 Champions League final more than his potency against Boro - but his eight glorious seasons at Stamford Bridge should be appreciated in its entirety.

The former Ivory Coast international came to Chelsea in 2004 for a £24m fee.

That was a lot of money for a player back in 2004 with the market going crazy since - but it was probably one of the best signings they have ever made.

He has safely secured his place as a Chelsea legend.

With Ayew leaving Swansea in the summer after his contract at the Liberty Stadium, Neil Warnock will be breathing a massive sigh of relief.

Why? Because the Ghanaian five goals in just four appearances against the Teeside club, including a brace last season in a 2-1 win for his side in Wales.

His second goal was particularly painful for Warnock's men, coming in the 97th minute via a penalty. However, football fans across the country would have predicted his departure if Swansea didn't achieve promotion - and they missed out by the smallest of margins.

Steve Cooper's men beat in-form Barnsley in the play-off semi-finals, with Ayew scoring in the first leg, before going down to a 2-0 defeat to Brentford at Wembley.

Barring a move to another Championship side or a cup meeting, the Boro and the forward won't face each other next season.

Happy days for Warnock and his men.

The Czech international had two sublime loan spells with Watford, where he guided the Hornets to promotion in the 2014/15 season and demolished several Championship sides on the way.

Those two seasons are the highlight of his career so far despite now playing in the Premier League with Burnley. Vydra also had spells with Derby County, Reading and West Brom in England but only played against Middlesbrough seven times.

Despite this, he scored five goals against them and at that rate, he is likely to bag himself even more goals if he came up against Boro again at some point.

With Burnley and Middlesbrough in different divisions currently though, any meeting would be in the Carabao or FA Cups.

Despite making over 200 appearances for the Whites and scoring 88 goals in the process, he will be remembered as a legend solely for being part of a side that beat arch-rivals Manchester United on their home turf back in 2010.

Against Boro, he struck five times in four games and seemed to make a habit of scoring against the Riverside outfit.

His partnership with Jermaine Beckford between 2008 and 2010 was a productive one before the latter's Premier League move to Everton - and Becchio remained with the club for three more years before moving on to Norwich City.

He left the Canaries and England two years later in 2015 before returning briefly with Rotherham the following year - but he failed to make a big impact at the New York Stadium and retired in 2017.

When you reminisce about the playing days of Barry, you think about his solidity in midfield and reliability, not his threat going forward.

With all respect to the 40-year-old, he received his England call-ups to be a barrier in front of the defence - but Middlesbrough fans are still having nightmares about him for a different reason.

This is because he scored five times and recorded two assists against them domestically across a long-lasting playing career.

Although he did appear against Boro 25 times, this is still a very impressive record for a defensive midfielder and he may be a surprise addition to this list, but he's totally worthy of his place in the top ten.