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3d A lot of difficult argument is most distressing (9). I have L?R?O?I?G

Are you sure of the 'l'? The answer looks like

Harrowing - distressing
Har(d) is 'a lot of difficult' and
rowing is 'argument'.

I'm pretty sure. It comes from 1a which is Former Wimbledon champion in Maryland is crushed (6). I made that "Milled" (Ille [Nastase] in Md). I agree that Harrowing works well but it gives ?i?h?d for 1a - and nothing useful results from that as far as I can see.

That might be M ASHE D if the i were wrong.

Thanks. Yes the "i" could just as well be "a" (At instead of In One Go).