Tottenham Hotspur players Micky van de Ven, Cristian Romero and Richarlison are unlikely to return from injury until the new year, manager Ange Postecoglou said on Wednesday.
Richarlison suffered a hamstring injury during Spurs' 4-1 win over Aston Villa last month while Van de Ven and Romero, who returned after injury layoffs in the 4-3 home defeat by Chelsea, did not finish the match due to fresh injuries.
Spurs play four more games this month, starting with Thursday's League Cup quarterfinal at home against Manchester United followed by three Premier League games.
"I think both (Van de Ven and Romero) will be (back) in the new year," Postecoglou told reporters.
"Not as significant an injury as last time with Micky but having a setback the medical team is going to make sure he is right to go."
Postecoglou said forward Mikey Moore, who has been out with illness since his last appearance in the League Cup match against Manchester City in October, has returned to training.
"Mikey is back in training. The next cabs off the rank are Mikey and Ben Davies potentially next week and Richarlison potentially the first week of the new year," he added.
Defender Destiny Udogie is also doubtful for Thursday's game due to fitness issues following their 5-0 win over Southampton while Yves Bissouma will return after serving a suspension.
"Destiny is still a bit sore from the game. We are not ruling him out but we will see how he is with the turnaround," Postecoglou said.
Postecoglou said United will pose a "big challenge" for Spurs in the quarterfinal as new manager Ruben Amorim has had a positive impact on the team since his arrival last month.
"He has obviously tweaked the formation a little bit, given different players an opportunity because he wants to have a look at everyone but as they showed at the weekend," he said.
"They are pretty tough competitors still. (I am) looking forward to meeting him and taking on the challenge tomorrow."