Source: Journals of the House of Lords (1610)

That whereas the House of Commons have already, among their Grievances, preferred a Petition to His Majesty, as of Right and Justice, That the Four English Counties may have a Trial by Law, concerning their Inheritance to the Common Laws of this Realm, and so to be exempted from the Jurisdiction of the President and Council of Wales (a Matter wherein the whole Realm is deeply interested) ; notwithstanding, upon Occasion of this great Contract, the House of Commons doth humbly petition His Majesty, as of Grace, that, without further Suit, Trial, or Trouble, those Counties may be restored to that their ancient Right, the same being no way prejudicial to His Majesty's Honour in Point of Sovereignty (as we conceive) ... (Kindly transcribed by Sven Yargs)

1. Would someone please explain how to determine/deduce the right meaning? All the linked definitions look apt to me. 2. Should there be an article where I placed a diamond?

If I pick definition 2a (= a state of affairs that provides a ground or reason), then that sentence becomes: 'notwithstanding, upon state of affairs of this great Contract, the House of Commons...' Yet this sounds grammatically and contextually wrong?

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    Perhaps you need a dictionary that gives archaic/obsolete usages. OED includes definition I.5 the action of causing or occasioning something. Also (in extended use): that which is caused or occasioned. Obs. If you want a term that can directly replace your cited usage (assuming it doesn't make sense to you to simply precede it by the definite article), perhaps implementation, occurrence, instantiation might work for you. In 1600 it probably didn't necessarily imply anything about occurrence for a specific reason. – FumbleFingers Oct 26 '14 at 15:24
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    The primary sense of occasion in EME was 'opportunity'; in this sense the word was more often used without an article than with one down to the middle of the 19th century. You can't argue from idiomatic use of one term to idomatic use of another. – StoneyB Oct 26 '14 at 17:02

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