Actually, Land Rover's own shop manual for the 4.4 liter engine instructs you to (in step-by-step order):
1 - Remove undershield (10 bolts)
2 - Remove oil pan drain plug and drain oil
3 - Remove radiator access panel (4 bolts)
4 - Remove oil filter and drain leftover oil
5 - Lube seal and tighten new oil filter to 18 Nm (13 lb-ft)
6 - Tighten drain plug to 25 Nm (18 lb-ft)
7 - Fill, check, top off, reinstall undershields, etc.
So, you can safely do it the old fashioned way (plug first, then filter), I'd do it that way as well.

I imagine that removing the oil filter before the plug may cause the oil to drain faster from the pan, although it could get messier in the beginning?