dair, who was born in dunfermline, began his career in 1991 with local fife team raith rovers. a first division winner in 1992–93, dair suffered relegation in raith's first season in the premier division. months into raith's season back in the first division, dair was part of the side that beat celtic to win the league cup, ensuring uefa cup football for the following season. buoyed by the cup success, raith won the title on the last day of the season and were promoted again at the first attempt. dair scored raith's first ever european goal, netting from close range against faroese team gí gøta and raith won through the first two rounds to face bayern munich, losing 4–1 on aggregate. unfortunately, raith suffered domestic relegation again and when manager jimmy nicholl left in february 1996 to join millwall, dair – along with stevie crawford and david sinclair – went with him.