Like most British Overseas Territories the Anguilla flag consists of a British blue ensign defaced with the territories arms:
While the use of ensigns at sea (which is where the flags were originally only meant to be used) is good. I think events like this highlights the impracticality of flags like this on land and at sporting events. For example a lot of countries and territories in the games use similar flags like this, these could be easily mistaken on a scoreboard.
I am of the opinion that Overseas territories at least should fallow the example of Gibraltar. At sea Gibraltar vessels use an ensign with the territories arms:
However on land and for sporting events a banner of arms is used as the territories flag:
As a result Gibraltar has a more distinct and recognisable flag than any other BOTs and has not lost any of its identify or sovereignty as some people might say in regards to changing flags.
Anguilla also has the advantage as it doesn't need a new flag, it could use the rather good Dolphin flag that was used when it declared independence from the former Saint Christopher-Nevis-Anguilla, in 1967 until it chose to regain UK sovereignty in 1969:
This flag is still in used in the form of arms on the current flag, and is still used unofficially today, so it is perhaps the best option for a flag in the Commonwealth Games at least.
To see the first Commonwealth Games Post click here, and remember to look out for the 'CG' in the title for future Commonwealth Games posts.