Shrewsbury Town players Danny Hall, Michael Symes and Neil Ashton have left the club.
Defender Hall, 24, has signed a permanent deal with Scottish side Gretna, while the other two players are joining Macclesfield on loan.
Striker Symes, 24, and defender Ashton, 22, will stay with the Cheshire club until the end of the season.
The two players are now training with Macclesfield and are expected to sign deals later this week.
Symes, who scored 13 goals for the club in 2006-07, had a brief spell at Macclesfield early in his career.
Defender Ashton has played more than 100 games for Shrewsbury since joining from Tranmere Rovers in 2005.
Neither of the players have been first-team regulars at the League Two club this season.
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