You mention Southend,so you will know they are the masters of it.they have done it for the last few years with paye and did in the last few months.Southend even set up a time to pay agreement last year with hmrc which is basically a last chance saloon kind of thing and they even negaged on that.and yet they still got the winding up order adjourned twice since before it was eventually sold.however they did receive a points deduction but that was done to none payment of wages.
Macclesfield was slightly different in they went into administration and relegated due to a points deduction for non payments of wages which included a tax bill but the national league won’t allow a club in the league who are in administration.so effectively they became insolvent and had to be wound up.