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There is no signage at the entrance of Highbury Station road to indicate the specific restrictions as they state

'At the entrance of Highbury....' is not the test. Did the CPZ entry signs carry this info?

You can see a map of the CPZs here
https://www.islington.gov.uk/-/media/sharepoint-lists/public-records/transportandinfrastructure/information/maps/20192020/20190501cpzmap.pdf?la=en&hash=279CB44454DF2CEC4601EBC639FF998C06463A97

The signs should be at the boundary of the zone you were in.

The traffic order defines match day as below as an event, and then the term match day is used throughout. I think this is a cop-out because Islington doesn't want to pay to update the signage. There is also the rather wooly definition of event (how would you know about 10,000+) and 'the Council deem should be treated'.

"match day" where referred to in the map schedule legend in relation to the
permitted hours, prescribed hours, restricted hours or no stopping hours, as
the case may be, of a parking place or loading place, or of a length of waiting,
loading or stopping restrictions, means a day on which an event is taking
place or which is planned to take place at the Arsenal FC Emirates Stadium,
Hornsey Road, London N7 which:
(a) under normal circumstances, would have an expected attendance of
10,000 persons or more, not including any staff or contractors engaged
in either the operation or management of the aforementioned stadium
or event; or
(b) is any other event at that stadium that the Council deem should be
treated as though it were an event specified in sub-paragraph (i) above
for the purposes of the application of the provisions of this Order;

Order:
https://www.islington.gov.uk/-/media/sharepoint-lists/public-records/transportandinfrastructure/parking/2023-consolidation-order/made-orders/charged-pps.pdf?la=en&hash=64698EEAAE1E4724745F00DDD948CE0FA6E5BAD5

There was no match at the stadium on that day. Words mean something on traffic signs.

A sort of related case below.

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Case reference   2240509048
Appellant   Mohammed Khan
Authority   London Borough of Newham
VRM   J444MRN
   
PCN Details
PCN   PN39339866
Contravention date   28 Jul 2024
Contravention time   16:16:00
Contravention location   Leytonstone Road
Penalty amount   GBP 80.00
Contravention   Parked for longer than permitted
   
Referral date   -
   
Decision Date   08 Jan 2025
Adjudicator   Edward Houghton
Appeal decision   Appeal allowed
Direction   cancel the Penalty Charge Notice and the Notice to Owner.
Reasons   I heard this appeal by telephone speaking to the Appellant’s representative Mr Dishman. His case is essentially that the sale of chicken does not amount to an event day and that the signage indicating the presence of an event day was in adequate. The onus is on the Council to prove that the day was an event day in law and that this fact was clearly and correctly indicated.
An event day is defined in the Traffic Management Order provided by the Council as (so far as is relevant to the present case) “any other sporting or non-sporting activity which in the opinion of the Traffic Manager for the London Borough of Newham is likely to benefit from the scheme being in force”. There seems to me to be no evidence from such a person that he/she formed that opinion. In the circumstances I am unable to be satisfied the day in question was an event day within the meaning of the TMO and the Appeal must be allowed on that ground alone.
(It is therefore unnecessary to consider whether the signage in place on the route described by the Appellant was sufficiently clear – something which might well have necessitated an adjournment for the Council and/or the appellant to provide photographic evidence of the particular sign passed and its location.)

I cited that case for fun - while some would much prefer chicken wings over Robbie Williams, I think he got far more than 10,000 for his show.

The point really is that while they've redefined match as event in the order, the basic test of signage at the bay stands as match.

It's 1-0 to the Arsenal, not Robbie (who is the president of the mighty Port Vale FC).

If it were me I'd go on with it but I would be happy to punt the extra £55 in a double or nothing gamble if they force it to the tribunal as I think an adjudicator would be persuaded by the word match and what you see on the top of the webpage Islington refers to.

Selfishly I'd like to see Islington tested on this.   

Please post up all sides of the NtO - just redact yr name & address - leave all else in.