Former Blues winger Cameron Stewart is on trial with League One Sheffield United, along with one-time Town loanee Reece Brown.
Stewart, 25, had his contract with the Blues terminated by mutual consent on the final day of the transfer window having made only two FA Cup substitute appearances in two years at the club.
Defender Brown spent time on loan at Portman Road from Manchester United towards the end of the 2012/13 campaign but made only one sub appearance. The 24-year-old was released by Bury in the summer.
"We’ll be speaking with Reece today,” Blades manager Chris Wilder told The Yorkshire Post.
"He’s done well, impressed us, and I’ve spoken before about the importance of having competition for places through the team.
"I’m not going to be sticking a gun to anybody’s head. But, like I say, he’s done well and so we’ll sit down and talk about something.
"Cameron is still here with us and he’ll play in a game. We’ll probably reach a decision on him at some point after that. We’ll see what happens there.
"Players can find themselves without a club for all sorts of reasons. They’ve both been given opportunities here and it’s a chance for one, potentially for both, to put their careers back on track.
"We tried to get another wide player in before the window closed, but we weren’t able to get anything across the line in time. That’s why we are taking a look at him, because that vacancy is still there.”
Sheffield United were among the other clubs keen on recruiting Grant Ward before he signed for Town from Spurs in August.