This is who I think the Freya Familia executives will fight in the War Game.
Gulliver Brothers: The Hostess of Fertility waitresses will fight them and win. Ryu will already be Lv5 after meeting Astrea, and the others will receive level boost.
Hogni: Tiona and Tione will probably fight him and win. But the twins will probably unable to continue fighting after this.
Hedin: Bell fight him but I doubt he can win by himself. Bell will solo against Hedin most of the time but eventually he will win after receiving help maybe from Ryu after she finishes fighting the Gulliver Brothers.
Allen: Bete will solo him at first but eventually loses. Ais will then have to fight Allen and defeats him.
Ottar: Finn, Riveria, Gareth and Ais will fight together against Ottar at first. Ais will later have to abandon fighting Ottar and move to fight Allen after Bete is defeated. After Ais leaves, Ottar eventually defeats Finn, Riveria and Gareth. Bell and Ais will fight together against Ottar in the end though I doubt it will be just the two of them against Ottar. Maybe some others will help after finish fighting the other executives and level boost will be given.