I haven't seen NR fight, except for the Esdeath vs. Akame one in the anime. But watching only the original version of Fate/Stay Night, this is my analysis...
- Lancer is fast, so is Assassin. But in simultaneous battle I don't know, since fights in F/S had a lot of stops. But if they were to keep fighting they'd cause NR to worry, especially with the bloodlust Lancer has.
- Herc is gonna be a huge (not intended) problem. Ten lives will drain NR's stamina, so it'd be best if they finish him last. But if they do, could they kill him ten times, with all his pesky teammates already having taken their stamina?
- Archer (I have to butt this in, is that really Emiya? SH*T!) can and will pick them off one by one. If Caster does provide unli mana for the team, Archer could spam UBW on NR one at a time. No worries.
- Caster will be the pivotal point here. Should she do her best supporting her teammates while wreaking havok, NR could become disorganized and be taken separately. Take note that she could warp space/reality, so the battefield's really a non-factor in this battle.
- And the magic picks: Saber and Rider. About Rider: if strategically used, her Pegasus could deal a lot of significant damage and initiate other teammates to finish the others not killed. Saber, on the other hand, could play the role of bait; being the most balanced, she could lead NR members into a tight space and finish them with Excalibur/Avalon combo.
Those are my thoughts about Servant team strategies, if you see any interesting openings just reply XD
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