Rangers have announced James Beattie has left the club while John Fleck, Kyle Hutton and Andrew Little have gone out on loan.
Beattie exits after failing to make the grade at Ibrox in just more than a year at the club having spent the second half of last season on loan at Blackpool.
He only made six starts in all competitions for the SPL champions.
Young midfielders Fleck and Hutton have signed for League One Sheffield United in deals confirmed by the SFA before the deadline.
Little, who has recently returned from injury, will play for Port Vale in League Two until January.
A statement on Rangers' official website read: "Rangers have done some last minute business in the transfer window with James Beattie leaving Ibrox and both John Fleck and Kyle Hutton going on loan."