IRON LEDGEROPPONENT CASE FILE
Ebisu fought Jiraiya and Pain from chapter 90 to chapter 426. Chapter 90 (episode 52): Jiraiya beat Ebisu. Chapter 426 (Shippuden episode 161): Pain beat Ebisu.
Jiraiya uses a toad to knock Ebisu out after Ebisu confronts him at the Konoha Hot Springs.
The chapter depicts Ebisu being incapacitated by Jiraiya, so this named encounter files as a win.
The Naraka Path interrogates two Konoha ninja and finds Konohamaru watching. Ebisu steps in so that Konohamaru can escape, is quickly overpowered, and refuses to say where Naruto is, and the Naraka Path moves to kill him.
Files W at CH. 426, where the chapter shows Ebisu quickly beaten by the Naraka Path. Konohamaru's rescue comes after the beating and does not undo it, and his own fight with the Naraka Path is a new pairing with its own depicted result. EP. SH-161's page lists CH. 425 to 428. The result stands for one of Pain's bodies, as the Hinata Hyūga CH. 437 row does.