do 10" contessas fit without needing flares on standard drums? The ones with a deeperdish ones, not with the centre flush with the outside.

Not quite. I've got them on my new white roundy which has flat faced drums on the front and 1/2" spacer drums on the rear. The tyres are 165 and they would be outside the guards without the flares. The smallest flares would cover them though.
M

If you have the deep dish contessas and regular drums (not cooper S spacered drums) then it should fit under with no flares?

I have LS contessas that are not deep dish and Cooper S brakes at the front with spacered drums at the back and no flares... I believe the difference in the dishes between regular contessas and LS contessas is exactl 1 inch which means logically they fit.

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Lillee - 1969 Morris Mini K