is not a great time to be selling players, mainly because of the problem in finding suitable replacements.

Clearly if Emmanuel Latte Lath was to leave Middlesbrough before this window’s transfer deadline, the club would have to move quickly and purposefully if they wanted to secure a replacement. The transfer uncertainty of bringing in the right type of replacements in January is probably the main reason why Boro have sold very few players during this month over the years, especially goalscorers.

On the other hand, sometimes the fee is simply too high to turn down. And if you have a potential replacement already lined up, then sometimes it might make sense. Arguably the club’s biggest modern era loss came in the January of 2010, when Boro sold Adam Johnson to Manchester City for a reputed fee of £7m.

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Boro had been relegated from the Premier League the previous summer, while in the October Gordon Strachan replaced Gareth Southgate in the hot seat. Johnson had been slightly in the shadow of England winger Stewart Downing in recent seasons, but the summer sale of Downing to Aston Villa allowed Johnson to come into his own.

In fact he was the man who made Boro tick from an attacking point of view. He was the only player consistently hitting the back of the net. Johnson had delayed signing a contract extension to come into effect at the end of the 2009-10 season. While there were reports that he wanted to move on.

New boss Strachan didn’t want to lose him but with City’s official offer burning a hole in the table, it was an opportunity for the Scot to use the cash to strengthen the squad as a whole. Chairman Steve Gibson would have expected Boro to mount a solid push for a quick return to the Premier League at that time, which was probably the main reason why Southgate was sacked.

Strachan clearly hoped to bring in the calibre of player who could revive the team’s prospects. They had slipped down the table somewhat despite Johnson top scoring with 12 goals. So Johnson was sold and Strachan went back to Scotland, where he had enjoyed remarkable success as Celtic manager. He brought in players that he knew well.

They included strikers Scott McDonald, Chris Killen and Lee Miller, along with attacking midfielder Barry Robson and Stephen McManus and Willo Flood. Unfortunately the plan did not work. Boro’s new look squad did not quickly blend together and the side struggled to challenge for a play-off place. They eventually finished mid-table.

The Johnson departure continued to have an effect after Tony Mowbray took up the reins from Strachan, whose tenure was ended after around 12 months. Boro’s failure to mount a promotion challenge had proved very costly and the club was suffering from financial problems.

As a result, in the following January, two of the most experienced and valuable players in the squad were sold. David Wheater, another like Johnson who had been with the Boro since he was a lad, moved on to Bolton Wanderers for a large fee. He went on to make 236 appearances for Wanderers over eight and a half seasons, some of which were spent in the Premier League.

At the same time Boro sold midfielder Gary O’Neil to West Ham United after four and a half seasons on Teesside. This cash influx probably went some way to helping balance the books but at the same time considerably weakened the squad.

In the Boro’s last season in the Premier League in 2016-17, Aitor Karanka allowed two strikers to leave the club in the January. They included Jordan Rhodes, who Karanka had bought 12 months earlier from Blackburn Rovers to try to ensure that Boro won their promotion battle.

Rhodes, who reputedly cost £10m, did reasonably well in helping Boro to reach the top flight when scoring six goals in 18 appearances. However, as far as Karanka was concerned, Rhodes did not appear to fit the bill for the club’s Premier League return.

Karanka went out and signed a top striker in Alvaro Negredo to lead the attack and the Spaniard did a reasonable job in a struggling side by scoring ten goals. However, Karanka’s defence-based, one-striker system meant that there were no regular openings for other forwards in the line-up. So Rhodes had little pitch time in the Premier League.

In fact, Karanka obviously felt that there would be so few opportunities for Rhodes that the striker was loaned out to Sheffield Wednesday in the January. The transfer was made permanent in the summer for a fee which probably fell well short of £10m.

At the same time that Rhodes left the club, so too did fellow striker David Nugent, who had top scored for the team during the promotion campaign. Nugent was initially signed from Leicester City for a reputed fee of £2m, with a further £2m to follow if and when Boro won promotion.

He did the business in helping to take Boro into the top flight, but, following the arrival of Negredo, made just four Premier League appearances for Boro. As a result, he was also regarded as surplus to requirements and was sold to Derby County for a reported fee of £2.5m.

This was the season when Boro struggled as a whole in the top flight, particularly in the opposition box. They amassed just a miserable 27 goals from their 38 games and were relegated in second-bottom place.

The following year, with Tony Pulis having taken over from Karanka’s replacement Garry Monk just after Christmas, there was a bit of a January clear-out. This included the departure of forward Martin Braithwaite on loan to Girondins de Bordeaux. The Danish international was a Monk signing in the summer and was a top player, but he never settled on Teesside.

As a result he was keen to get away long before the move to Bordeaux was finalised. It was a pity to see him leave because of the positives which he offered the team. But it was out of everybody’s hands. Boro also sold midfielder Adam Forshaw to Leeds United for £4.5m that January, which was a good bit of business, while Cyrus Christie joined Fulham for a small fee and disappointing midfielder Adlene Guedioura joined Nottingham Forest on a free transfer.

The departures did not bring overall negativity because Pulis kept Boro on the straight and narrow. They went on to finish in the play-offs, albeit eventually losing in very disappointing fashion to Aston Villa in the semi-finals.

One of Michael Carrick’s first squad decisions was in allowing striker Duncan Watmore to join Millwall for a small fee in January 2023. Watmore had joined Boro on a free from Sunderland two years earlier after recovering from a major injury. He did well on Teesside, top scoring with nine goals during his first season here. Again, at the end of the season in which Watmore left, Boro finished in the play-offs, though it was another frustrating semi-final exit, this time at the hands of Coventry City.

Twelve months ago we might not have expected Aston Villa to come in with a £10m offer for Morgan Rogers, who was playing well for Boro but not necessarily seen as the key player in the side. It was a good piece of business and well done to Rogers, who has fully established himself in the Villa line-up and won two England caps to date. Boro though, ended up falling short of reaching the play-offs for a second successive season.