It looks like this sequence is the batch of charts received the day before we set off.  

So, the first one is saying that nothing interesting is going to happen on Saturday (aka "today")

Then this one looks at the day of the ride (timed almost as we start at 0630). It confirms that in England we will have southerly winds.

Next, this shows the situation when we're somewhere like Grantham.  Decent following winds.

And this one shows that by midnight (in southern Scotland) we'll be hit by the cold front.   If you check the report, you'll find that we got showered on and the wind was less useful.   But let's not be ungrateful, because the weather was really good for the first 12-14 hours and then okay for a bit longer.  It was certainly helping us as we made our way up to Carter Bar.