Hi Sohaib,
Sorry for such a late reply.
If you are still interested – the first thing that comes to mind – the plugin must be enabled at the time order gets its initial status. If you open order’s admin edit page, you should see the “Order Status History” meta box – it should say that there are some records of status change (vs empty status history).
Also, to solve the problem with empty status history – there is “On empty order status change history” option in “WooCommerce > Settings > Order Status Rules > Advanced” – try setting it to “Use order date created” or to “Use order date modified”.
And again, sorry for such a late reply.