▁( when ▁United ▁were ▁tro phy less ▁for ▁only ▁the ▁second ▁time ▁in ▁the ▁de cade ) ▁before ▁making ▁his ▁final ▁two ▁appearances ▁in ▁the ▁ 1 9 9 9 – 2 0 0 0 ▁campaign , ▁when ▁United ▁won ▁their ▁sixth ▁title ▁in ▁eight ▁seasons , ▁but ▁once ▁again ▁C leg g ▁failed ▁to ▁meet ▁the ▁required ▁number ▁of ▁appearances ▁for ▁a ▁title ▁winner ' s ▁medal . ▁ ▁C leg g ▁spent ▁time ▁on ▁loan ▁at ▁I ps wich ▁Town ▁and ▁W igan ▁Athlet ic ▁before ▁he ▁joined ▁Second ▁Division ▁club ▁Old ham ▁Athlet ic ▁on ▁a ▁free ▁transfer ▁on ▁ 1 9 ▁February ▁ 2 0 0 2 . ▁In ▁his ▁first ▁season , ▁he ▁played ▁just ▁ 1 0 ▁times ▁as ▁Old ham ▁qualified ▁for ▁the ▁Second ▁Division ▁play - offs , ▁only ▁to ▁see ▁them ▁be aten ▁in ▁the ▁semi - final s . ▁A ▁potential ▁purchase ▁of ▁the ▁club ▁fell ▁through ▁and ▁they ▁went ▁into ▁administration , ▁resulting ▁in ▁the ▁squad ▁being ▁g utt ed ▁to ▁cover ▁their ▁deb ts . ▁C leg g ▁remained ▁with ▁the ▁club ▁and ▁played ▁ 3 2 ▁times ▁as ▁they ▁finished ▁in ▁ 1 5 th ▁place ; ▁however , ▁he ▁strugg led ▁with ▁his ▁mental ▁health ▁and ▁retired ▁from ▁professional ▁football ▁at ▁the ▁end ▁of ▁the ▁ 2 0 0 3 – 0 4 ▁season . ▁ ▁Co aching ▁career ▁After ▁two ▁years ▁out ▁of ▁the ▁game , ▁C leg g ▁was ▁appointed ▁by ▁former ▁Manchester ▁United ▁team - mate