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Sadly older but none the wiser (8)

(older but)*
Troubled as in vexed

Strange but loser grumbles (8)

clue is for `troubles`

Hung back from rough and tumble gone mad - chaotic mess results (7)
(ROUGHANDTUMBLE - HUNG - MAD)*

Taking a bit of a liberty perhaps using “back” and “gone” as the subtractive verbs. Pity “mad” didn’t quite do double duty as the anagram indicator as well, hence “chaotic”.

Literally a middle name to annoy (7)

Scared old tuber (8)

This first currency was part of Irish history(8)

troubles

Russian dosh in Yorkshire causes upset (7)

t'rouble (apologies to people from Yorkshire!)

Blunt & Igor connive - worrying for the UK (9)

(BLUNT + IGOR)*

Bit dated perhaps- Sir Anthony BLUNT - curator of the Queen’s pictures - was unmasked as a Russian spy.

Blue? Sort out your problems! (8)

Problem: 160 + 80 x 2 - 500 (7)

T R DOUBLE-D

Medieval Roman numerals! Woooooooooooooooo!