Ange Postecoglou and Tottenham have been dealt a devastating blow following the news that Micky van de Ven and James Maddison will be out of action until 2024. Two pivotal players in Spurs' excellent start to the campaign, both came off with injuries in the first half of Monday's 4-1 defeat at home to Chelsea.

Maddison was substituted with an ankle issue after going down in the Chelsea box under no contact just prior to half-time, with Van de Ven struggling to make his way off the field after pulling up with a serious hamstring injury. Tottenham fans have been sweating over the extent of the duo's injuries ever since and on Friday Postecoglou delivered some bad news in his pre-match press conference ahead of the trip to Wolves.

Asked about winning his third Premier League Manager of the Month gong and for the latest on the injury front, he said: "Yeah we don't get a lot of time to enjoy the moment, do we? I'm glad you put it in there but let's get onto the real stuff. No, all good. Fair to say there was a fair bit happening after Monday night.

"If I can go through them... Micky Van de Ven with a hamstring injury we knew was fairly significant. Probably a couple of months for him - looking into the new year.

"Madders, a lot worse than we thought. He came off with the ankle injury, but the next day wasn’t great so we sent him off for a scan. So again not great for him and probably into the new year for him.

"Richy had the operation, which we’d kind of scheduled anyway because Richy has been battling with it from day one and we thought with the international break coming up we thought it would be a good time to get it done. He should only be a month if everything goes well so not too long after the international break.

READ MORE: Ange Postecoglou issues worst Tottenham injury news on James Maddison and Micky van de Ven

READ MORE: Ange Postecoglou has wildcard James Maddison replacement option after Tottenham injury update

"They’re the main ones, obviously we have a couple of suspensions as well. [Ben] Davies is back and available. [Pedro] Porro’s fine."

So what games will Van de Ven and Maddison miss over the next couple of months before they return to action early next year? football.london takes a look below.

Taking on Wolves on Saturday before the third international break of the season takes place, Tottenham have a number of mouth-watering games on the agenda when they return to domestic action. Hosting high-flying Aston Villa first up, the team then travel to the Etihad Stadium the following weekend to take on Premier League title holders Man City.

Postecoglou's men then have home games in quick succession against West Ham and Newcastle United, before playing Nottingham Forest away and Everton at home in their final games prior to Christmas. Tottenham's festive schedule sees them visit Brighton & Hove Albion on December 28, with a home game against Bournemouth on the calendar three days later.

Tottenham then start 2024 with an FA Cup third round clash on the weekend of Saturday, January 6. Their first Premier League match of the new year comes against Manchester United on January 14, which could possibly be the game Maddison and Van de Ven make their comebacks in depending on how their recoveries go.

If not, both will be hoping to play some part in a potential FA Cup fourth round game on the weekend of January 27 or three days later when Brentford travel across the capital to Tottenham Hotspur Stadium.

Tottenham's upcoming fixtures

11/11 - Wolves (A) 12.30pm

26/11 - Aston Villa (H) 2pm

03/12 - Man City (A) 4.30pm

07/12 - West Ham (H) 8.15pm

10/12 - Newcastle United (H) 4.30pm

15/12 - Nottingham Forest (A) 8pm

23/12 - Everton (H) 3pm

28/12 - Brighton & Hove Albion (A) 7.30pm

31/12 - Bournemouth (H) 2pm

06/01 - FA Cup third round TBC

14/01 - Manchester United (A) 4.30pm