I didn't see the starting distance...Perhaps Jiraiya does solo after all.
I think Gaara would have difficulty restraining huge boss summons with enormous leaping power, and they can break free from his sand restraints (plus sad can be disabled with toad oil.) Great Shark Bullets could be troublesome but I don't think Kisame can rapidly fire off multiple GSBs without a rest interval and Gamabunta can probably dodge them. Boss summons buy Jiraiya time to set up his Toad Confrontation Chant.
Kisame and Gaara could win this actually if their teamwork is good.
Gaara was able to restrain leg Susannos against madara none of his summonings has shown strength of leg Susanno or defenses either while Jman is charging up sage mode which took mad long Gaara can easily creates a desert which only takes about 1 min - 3 min
Kisame can also send that shark thing he did to kisame at anything jariya throws at them that's elemental and can target his toads as well gaara can crush toads legs easily and Jman can't really touch Gaara or kisame in air
Also once again what is stopping kisame from creating a huge ass water dome trapping team 2 inside it should b longer then 2 miles at least Thts what It looked like don't quote me on tht tho ? Jmans toads can't save him they can't breath underwater look it up
Chiyo is non factor she is easily dispatched
While kisame is fused with sameheada in his water dome against team 2 Gaara could b summoning more sand
Or what if Gaara does multiple sand tsunami's while kisame is closing the distance getting over there and then does hidden mist neither of team 2 can dispel it Gaara can then use sand sensing to attack team 2 while kisame can do silent killing espcially with his clones we seen how powerful they r
There is no way in hell sage jariya is soloing both kisame and Gaara he has a hard time with either as it is -.-