Hi Jason - many thanks
The entries are dated the same as that was when the property was first registered. That application will have included details of the 1916 Lease and the 2000 Transfer was the deed that triggered the need to register for the first time
We wouldn't know what the 'thinking' was behind the 2000 transaction
The fact that the freehold is registered with a noted lease does not mean that the lease has come to an end, been determined or bought out.
If they did buy the freehold and already owned the lease then the latter would only come to an end if they requested merger for example.
Practice guide 26: leases – determination - GOV.UK
I'd suggest seeking legal advice