The only way Chequered Flag ever loaded for me was if I stopped the tape half way through the loading, rewound it a bit, then hit play again.
I don't know how I discovered this, but I do find it amusing to this day that I didn't find it odd at all.
That's just how it was having a Speccy. You learned to be creative to get things working.
(Like my level skip cheat for Operation Wolf. It involved rubbing my socked feet across the keyboard until it gave the message it was skipping to the next level).