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No. Winsford was at the convergence of a four track section into a double track, not the end of a loop. So trains could be approaching in both tracks at the same time.
Indeed, and in addition to your excellent explanation, there can also be a timer, which does not allow the route to be cleared for the main line until a couple of minutes since the looped train arrived have elapsed, so minimising the risk of the looped train passing a signal at danger and entering the main line just as the overtaking train approaches.
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