This is tricky as there's no agreed definition of Scottish; obviously one cannot base it on accent. The most obvious test of being Scottish is having been born in Scotland.
There have been a number of Scottish PMs since 1945:
Several pre-WW2 PMs were Scottish (e.g. Ramsay Macdonald, Arthur Balfour and Henry Campbell-Bannerman). They were all Scottish born.
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There have been 74 Prime ministers of Great Britain and Northern Ireland up until the 2010 elections. That is how many Election there have been. There have been 53 Prime Ministers that are different.
Collingwood won the VFA premiership in 1896. It's first VFL/AFL premiership was in 1902.
Since 2000, Manchester United have won the Premiership 6 times.
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Mainly Arsenal, Chelsea and Manchester United.
Chelsea has won the Premiership twice, in 2004-5 and 2005-6.