After featuring heavily for the Newcastle United in the last three seasons, it has been a disaster this time around for Matt Ritchie.
The injury occurred in the Carabao Cup second round at St James' Park, where Leicester City needed penalties to overcome Newcastle after a 1-1 draw.
Ritchie hobbled off after a challenge from Hamza Choudhury in the second half, and since then it has been bad news.
Ritchie's long absence has handed the opportunity to summer loan signing Jetro Willems, and the silver lining has been that the Dutchman has taken his chance at left-wing back.
Impressive performances against Manchester United and West Ham United have delighted fans, but the presence of Ritchie in the squad has undoubtedly been missed.
The versatility that made him a regular under Rafa Benitez and the fight that makes him an unwanted opponent is tough to replace from the squad completely.
Out until 2020
The road to recovery has been tough, and it was looking promising when the ex-Bournemouth man was due to return to training not long after the incident.
But setbacks have extended time on the sidelines and a first operation was required in October, and now he has undergone a second procedure.
A statement on the club's official website read: "United can now confirm that Matt Ritchie has undergone a second operation on the ankle injury he sustained during the Carabao Cup clash with Leicester City in August."
With a comeback set for January, there is still a chance he could play an important part in the second half of the season for Steve Bruce.