Scenario 1:
-Asuma was getting manhandled by Hidan, so as far as I'm concerned, his Taijutsu is lesser to his opponent. He gets stomped.
-Base Jiraiya from what I recall has no Taijutsu feats that suggests he could win. He was getting beaten by armless Orochimaru, and even his SM at best was blinding Ningendou Pain. Tendou Pain was twisting his arm with pitiful ease.
-Kakashi, on the other hand, was progressing in Taijutsu throughout the series. The beginning of Shippuden, he was stalemating Hidan easily; at Pain Arc, he and Tendou Pain were shown to be equal in CQC; in the War Arc, he stomped Obito in CQC. He can actually open 1 Gate, and demonstrated far better CQC feats than Jiraiya and Asuma ever have.
Kakashi wins scenario 1. Scenario 2 also goes to Kakashi, since Raikir is stronger than Chidori which is equal to Rasengan.