Dirk Lehmann springs to mind but I would imagine we've had a fair few since then!
The malaise of Scottish football is a consequence of the changing profile of our English football clubs, England and English football isnt fairing too much better either.
Up until the 1990's English football were awash with Scots, from kitman, coaches, managers, players, scouts with a healthy smattering of Irish too.
In many ways these became the power brokers in terms of recruitment and retention, they inevitably used their trusted confidante's in the process, nearly always fellow scots or Irish to drive decisions on players opportunities.
Of course nowyou have a United Nations of nationalities within a football club and the inclination not to look beyond only the very best in these countries means that opportunity has reduced for the good/solid Scots/Irish player that otherwise existed.
I doubt whether Cork or Glasgow was ever a hotbed of talent, moreso a hotbed of opportunity driven by their compatriots residing here in England.