 By mid @-@ October 1998 , York were placed eighth in the Second Division . They slipped to the bottom third of the table after winning one point from a possible twenty @-@ one . Despite improved results over Christmas , York played eleven consecutive matches without a win . In mid @-@ March 1999 , the club was just above the bottom four places , when Little was sacked and player @-@ coach Neil Thompson appointed caretaker manager . A flurry of transfers , including the departure of leading scorer Richard Cresswell to Premier League side Sheffield Wednesday for a club @-@ record fee of £ 950 @,@ 000 , followed . After losing away to Manchester City on the last day of 1998 – 99 , York dropped into the bottom four for the first time that season , and were relegated in twenty @-@ first place . The club 's trading loss for the season was £ 483 @,@ 096 , despite a record profit of £ 1 @,@ 274 @,@ 202 from lucrative transfers . Club historian David Batters said , " the stark reality was that the club had to sell to survive " . In July 1999 , the club and its real property assets , including the ground , were transferred to a holding company called Bootham Crescent Holdings ( BCH ) for £ 165 @,@ 000 . Thompson was sacked in February 2000 after a run of one win from twelve matches during the middle of 1999 – 2000 . Former Hull City manager Terry Dolan took over , and York finished the season in twentieth place after conceding only five goals in the last twelve matches . Losses for the season were £ 667 @,@ 255 , and the wage bill of £ 1 @,@ 635 @,@ 736 was twice that of 1995 . 
