Tottenham have allowed Kazaiah Sterling and Anthony Georgiou to leave the club on loan until the end of the season, despite both players carrying injuries.
Sterling started the season on loan with Doncaster Rovers, while Georgiou was with Ipswich Town, but both deals were cut short due to injury.
Sterling picked up what looked to be an innocuous dead leg injury at the start of September and has not played since.
Georgiou, meanwhile returned from a loan at Ipswich with a hamstring injury and both players are still sidelined.
Both players made their Tottenham debuts under Mauricio Pochettino, Sterling playing in the Champions League and FA Cup and Georgiou in the Champions League.
Tottenham have now confirmed that they have struck a deal with League Two side Leyton Orient for Sterling and League One outfit Bolton Wanderers for Georgiou.
There was interest from higher up the Football League for the highly rated Sterling but the decision was made to agree to the Orient deal because of his injury situation.
Both players are expected to be out of action until March at the earliest which would mean a maximum of 10 or 11 games if they were to return at the beginning of March, according to football.london.