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Win on board following heart from Madison Keys? (7)

Ross

I believe the answer is:

islands

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'madison keys?' is the definition.
'islands' can be an answer for 'keys?' (I've seen this before). I am not certain of the 'madison' bit.

'win on board following heart' is the wordplay.
'win' becomes 'land' (both can mean to secure or obtain).
'on board' means one lot of letters goes inside another (inserted letters are taken on board).
'following heart' becomes 'iss' (I can't explain this - if you can you should give a lot more credence to this answer).
'land' put within 'iss' is 'ISLANDS'.

'from' is the link.

Can you help me to learn more?

(Other definitions for islands that I've seen before include "Ibiza, Corfu etc" , "Land masses surrounded by water" , "Lad sins when surrounded by water" , "Eg, Faroes" , "Eg, archipelago" .)

I've seen this clue in The Guardian.
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