Youngsters Antonio Murray and Chris Hogg could join former Town coach Tony Mowbray at Hibernian. Mowbray, appointed manager at Hibs last summer, is keen to assess the pair as he seeks to strengthen his squad.
Murray is already at Easter Road and if he impresses could move to the third-placed Scottish Premier League side on loan for the rest of the season or even permanently. The midfielder's Town contract is up at the end of the season and the Blues may not be willing to offer the 20-year-old a new deal.
The Cambridge-born player has made one senior Town appearance, coming on as a sub at Derby on the final day of the 2002/03 season. His time at Portman Road has been interrupted by a succession of injuries.
Mowbray, whose assistant at Hibs is another Town man Mark Venus, says these problems have hindered Murray's development: "Antonio is training with us for a few days. He's a young boy who hasn't progressed as much as he probably should have for a player of his ability.
"I want young hungry footballers, so it's a chance to assess if he falls into that bracket and it is also a chance for him to have a look at the club and the city."
If Mowbray wants to sign Murray either on loan or permanently, the deal would have to be completed during January. Switches from Championship sides to Scottish clubs are not subject to the Football League's transfer window exemption.
Central defender Hogg is also interesting Mowbray but is out of action at present after injuring his arm warning off car thieves over Christmas. The Middlesbrough-born player is not expected to be back in action for six weeks, so a potential move to Hibs would have to wait until the summer.
Hogg joined the Blues from York City in 2001 for a fee which could eventually have reached £150,000 depending on his progress at Town. However, despite England calls at various youth levels, the 19-year-old has failed to advance as was hoped and will be released in the summer when his contract ends.
If Murray and Hogg make the move to Easter Road they will join former Academy colleague Sam Morrow who signed for Hibs in the summer.