More than six months on, Shaw remains at Manchester United and Barkley at Everton, but time is fast running out.
The pair appear to have worn out their welcomes, and are both claimed to be keen on transfers to Tottenham Hotspur.
The Sun report Shaw is desperate to reunite with manager Mauricio Pochettino, with who he worked successfully at Southampton, earning his big money move to Manchester United.
Both players are talented stars who have represented England, but both are also 'projects', talents in need of an arm around the shoulder and close guidance to try and get them back to their best.
Can Tottenham afford to bring them both in?
This is not just a question which applies financially, but in terms of management.
The pair each need close attention, which Mauricio Pochettino and his staff can provide, but whether they are ready to bring both in mid-season is another matter.
Shaw and Barkley are players who may not be ready to contribute straight away, and could need a full pre-season behind them if they are to make an impact for Spurs.
Of the duo it is Barkley's midfield position which is more pressing, if Victor Wanyama and Mousa Demble's injury problems persist.
Shaw's chances of making a move to Spurs will depend on Danny Rose's future at the club.
This could leave Spurs deciding to bring in just one of them at the most in January, and leave the other waiting anxiously to see whether they will clinch their preferred move to North London.