Answer: Caledonian
Caledonian FC won 15 Highland League titles from the 1900/01 season to the end of the 1999/00 season. Their first came in 1901/02, followed by further successes in 1910/11, 1913/14, 1925/26, 1930/31, 1950/51, 1951/52, 1963/64, 1970/71, 1976/77, 1977/78, 1981/82, 1982/83, 1983/84 and their last before departing for the Scottish Football League was in 1987/88. Elgin City and Clachnacuddin both have 14 Highland League titles each, Clachnacuddin winning the first of the new century in 1900/01. Elgin City should have had 15 along with Caledonian, but the title they won in 1992/93 was withheld by the Highland League association and no champion was recorded for that season. Buckie Thistle have won 8 Highland League titles during that time, while Inverness Thistle won 7 Highland League titles before their merger with Caledonian in 1994. Peterhead, who won 5 Highland League titles before their move into the Scottish Football League, won the final Highland League title of the 20th Century, beating Huntly by four points to take the title at the end of the 1998/99 season.