10 Sales in Football That The Big 6 Will Regret The Most (RANKED)

10 Sales in Football That The Big 6 Will Regret The Most (RANKED)

Over the last few years, the ‘big 6’ in the premier league have had some sales that they have lived to regret. Some of these might have not been straight away, but the player has grown and developed and ended up causing the club regrets for ever letting them go. We will be looking into the 10 players the top 6 have regretted selling the most and see what club has the most regrets.

10 – Scott McTominay (Manchester United – Napoli)

The 28-year-old has been incredible for Napoli ever since he joined them in the 24/25 season even winning the Serie A MVP last season. The Scot has managed to truly find himself in Italy and is definitely making United regret ever selling him.

Coming from the academy, he played 8 seasons for United and never managed to find the level he has found in Italy; however, he did show talent especially when in front of goal. It seems that United might have been playing him in the wrong position and might now be regretting selling him. They might be especially regretting it after the season they had after his departure. The Scott would’ve added physicality and goals something they struggled with last season.

One of the biggest regrets they could be facing as well, is the loss in value having sold him for £25 million. After joining Napoli his transfer value has doubled, this on top of the fact that he has become one of the best midfielders in the league, has caused United some regrets.

9 - Jamal Musiala (Chelsea – Bayern Munchen)

This one is a bit different to the other players that will be named on the list; however, it still is a massive regret. Originally from Cobham, Musiala was one of the best talents in Chelsea and for England, however, in 2020 he would end up joining Bayern. However, this wasn’t at fault of the club, Musiala’s mum had fears over her career in London as a result of Brexit. So, they ended up moving back to Germany and the 16-year-old Musiala had to leave.

Once again, this isn’t a regret of the club directly as they didn’t have a say over him leaving, however, getting £200,000 as compensation will sting especially as the now 22-year-old is one of the best creative players in the world and worth 700x the amount of what they got 6 years later.

8 – Trent Alexander-Aronld (Liverpool – Real Madrid)

The right back cemented himself as one of the best fullbacks in the world at Liverpool, however, they couldn’t get an agreement on a new contract last season, and this allowed him to depart as a free agent. Once again, a different type of regret and departure.

This time Liverpool’s regret comes from failing to have gotten a fullback that can cover for him at even close to his capability. This has been shown especially this season so far where Liverpool have struggled to even get close to matching last season. By the end of the season Liverpool will definitely regret letting their academy boy go especially on a free.

7 – Cole Palmer (Manchester City – Chelsea)

Once again, we see a player leaving the club where they grew and developed and it has hit back at his original club. In 2023 Cole Palmer left Man City for Chelsea for £41 million. Many people questioned Chelsea and thought City had gotten a phenomenal deal, until the end of the season where Palmer picked up PFA young player of the season with 40 goal contributions. City found themselves regretting selling one of the best academy players they had at the time.

Now City look to be regretting it even more having struggled to find that replacement for De Bruyne who many at the club thought Palmer would end up being. While they have signed some players who they are looking at replacing him, none of them have been able to get close to the once City boy. The £41 million Chelsea paid now seems like a steal and City will definitely be regretting ever letting him go, however, it does seem like Pep always knew they would regret it.

BREAKING 🚨: Chelsea sign Cole Palmer for £40m with a further £2.5m in add-ons! ✍️🔵pic.twitter.com/cWCoMBmgM8

— Sky Sports Premier League (@SkySportsPL) September 1, 2023

6 – Gareth Bale (Tottenham Hotspur – Real Madrid)

Spurs will definitely regret selling Bale as he was absolutely would class with them, being one of the best talents in the world. However, in 2013 Real Madrid came knocking for the Welsh man and he answered. They paid a world record £85 million for him to land the signature. While it was expected that Bale would end up leaving Spurs for bigger and better things, they would still regret it becoming one of the best forwards of this generation. The main regret would come about from trying to find a replacement. The main replacement that they bought in for him was Argentinian Erik Lamela, who never got close to the levels Bale had with Spurs.

The North London team will definitely believe that with him alongside other forwards such as Harry Kane and Son, they would’ve seen a trophy and much more success. So, while they did get a vast fee for Bale, the player that they lost and the players they signed to replace him have caused regrets.

5 – Cristiano Ronaldo (Manchester United – Real Madrid)

One of the greatest ever players, as expected has teams regretting ever losing him. Manchester United have definitely regretted losing the forward as he went on to develop and grow into one of the greats of the game. The main reason for him not being placed higher is the few that they received. Similar to Bale, United got a vast fee for him. United received £80 million in 2009 for the Portuguese forward. The other reason for it not being higher was the fact that it was expected that he would leave with many people knowing it was his dream to play for the Spanish giants.

This is why he can’t place any higher, while it is a massive regret to ever lose a player who has carried on in his career to become one of the greatest players to have ever graced the pitch, the expectation for him to leave and the fee received reduced the regrets that United would go onto have.

4 – Luis Suarez (Liverpool – Barcelona)

Once again, an English club losing one of their main men to a club in Spain. Barcelona paid £75 million for the Liverpool striker in 2014. He would once again, go on and carry on becoming one of if not the best striker in Europe and this generation. The main regret for Liverpool comes once again with who they replaced the striker with. Suarez left after a record-breaking season scoring 31 goals for Liverpool, so the reds would always struggle to find a replacement. However, spending £20 million on Mario Balotelli did cause regrets, especially after scoring 4 goals in his only season.

BREAKING 🚨: Chelsea sign Cole Palmer for £40m with a further £2.5m in add-ons! ✍️🔵pic.twitter.com/cWCoMBmgM8

— Sky Sports Premier League (@SkySportsPL) September 1, 2023

Once again, a top club losing a player who was one of the best in the world for the club but was expected to leave at some point does cause regrets, but the replacement signings are what causes the more serious regrets for the clubs.

3 – Luka Modric (Tottenham Hotspur – Real Madrid)

One of the greatest ever midfielders leaving your club will cause regrets, however, it did take a few years for Spurs to truly regret losing the midfield maestro. The now 40-year-old has had an incredible career especially as Los Blancos. Winning the Ballan d’Or was the pinnacle of his career. There are many reasons why Spurs would regret losing him with the main one obviously being he is one of the great midfielders ever and someone who would’ve helped them to reach success similar to Bale.

However, the main difference to Bale was the £50 million difference in their transfers. Real Madrid paid roughly £31 million for Modric from Spurs, and this would be something they would definitely live to regret as the midfielders becomes one of the most valuable players in Europe. Similar to the first few names, Spurs will regret this because of the loss in money, however, combine that with the previous names in losing a world class player, you have a team massively regretting selling a player.

2 – Mohamad Salah (Chelsea – Roma)

This is the first move where the club didn’t directedly regret selling the player as while Salah did do well at Roma, he wasn’t amazing, or not enough for Chelsea to regret selling him, yet. Then in 2017 Liverpool signed him and this was where Chelsea would regret selling the Egyptian. In his first season for Liverpool, he would hit 58 goal contributions and help Liverpool fight for the league. However, this was far from the last thing he would do. Every season he has played for Liverpool he has contributed over 30 goal contributions.

Chelsea would regret this for several reasons. One, they lost one of the greatest Premier League players ever. Two, they only received £15 million from Roma at the time when they sold him. Three, they gave Liverpool a player who would ultimately win them a Champions League as well as 2 Premier League titles. This is definitely one of the biggest regrets in the league, especially as he gave success to a league rival.

1 – Kevin De Bruyne (Chelsea – Wolfsburg)

Once again, we see Chelsea on the list and once again it’s another player who they sold and ended up coming back to the Prem as a world beater. De Bruyne spent 10 seasons with Manchester City and made himself one of if not the greatest creative midfielder that the Premier League has ever seen. While Chelsea did end up making more money from selling De then Salah, then success that he has bought a rival club is drastically more then what Salah did for Liverpool.

In those 10 years he played for Manchester City De Bruyne won 19 major trophies including 6 Premier League title as well as Manchester City’s first Champions League trophy. Overall, based on success, transfer fee, and ability of the player, losing Kevin De Bruyne is the biggest regret in the Premier League.