Conor Gallagher began his football journey at Chelsea’s youth system, but he was unable to cement his place in the first team and was loaned out to Charlton, Swansea, West Brom, and Crystal Palace.
After his successful loan stint at Crystal Palace, he returned to Chelsea, but again couldn’t get consistent first-team game time; the next season, Atletico Madrid signed him for around £33M.
At Atletico Madrid, Conor Gallagher was in and out of the squad due to fierce competition in the midfield position, but he still managed to make 77 appearances in all competitions and contributed to 14 goals.
In order to get more consistent game time, the 26-year-old returned to the Premier League and signed with Tottenham Hotspur for approximately £34M on a 5 and a half year contract.
He made 18 appearances in all competitions and contributed to 2 goals, while becoming one of the most trusted members in Roberto De Zerbi’s side, and helped Spurs avoid relegation to the Championship.
However, it seems that after just one season at N17, he could leave in the upcoming winter transfer window after falling down the pecking order due to the arrivals of Sandro Tonali and Mateus Fernandes.
This term, Conor Gallagher has made 8 Premier League appearances, but only started three games in the starting lineup, mainly coming off the bench during the final moments of matches and often playing out of position.
Despite his limited involvement in Spurs first-team under boss Roberto De Zerbi, Everton, Leeds United, and Aston Villa are keen to sign him in the upcoming winter transfer window.
🚨#Tottenham Despite interest from Everton, Leeds United and Aston Villa, Tottenham Hotspur appear determined to keep Conor Gallagher at the club. 📞 The midfielder continues to be viewed as an important part of the squad by both the club and the coaching staff. 🔄 Head coach Roberto De Zerbi is keen to retain Gallagher ahead of the January transfer window and does not want to weaken his squad. ⏳ As things stand, Tottenham are not believed to be actively considering a departure for the England international despite external interest.
— Ekrem KONUR (@Ekremkonur) November 9, 2026
Tottenham Hotspur manager Roberto De Zerbi still considers Conor Gallagher an important member of the squad and wants to retain him in the upcoming winter transfer window, as his departure will weaken the first-team.
However, Keith Wyness believes that Conor Gallagher is stuck in a repeating pattern, and a loan-to-buy deal could be on the cards for the England international in January.
The former Everton CEO highlighted that despite Conor Gallagher failing to settle down at multiple clubs, he is a talented player and his market value is still in the range of £25M to £30M.
Wyness told Football Insider (via Yahoo Sports): “I thought he was going to do really well at Atletico Madrid. Didn’t quite work out. He’s had a loan at Crystal Palace. He was very much loved there and did a great job. I like him as a player.
“I think he’s got a talent, but it doesn’t seem to pay off in terms of stability. I think they’re going to have to look at a loan in January, with an option to buy probably somewhere between the £25m to £30m mark.
“This pattern keeps repeating itself, and I can’t understand why. I think it’s going to have to be a loan in January, I’m afraid, and that will be another repeated pattern in Gallagher’s career, which is strange.”
Conor Gallagher’s contract with Tottenham Hotspur runs until 2031, and Spurs face no pressure to sell him in the upcoming winter transfer window, but the 26-year-old could move from N17 on loan to rejuvenate his career.
