1. Jiraiya: Jiraiya, one of Konoha's legendary Sannin, ranks equally with Itachi at a power level of 71. Although Jiraiya could potentially put up a good fight against Itachi, he acknowledged his inferiority and retreated from battle when faced with Itachi's strength.

2. Sasuke: Itachi, despite being significantly stronger than Sasuke, never desired to engage in combat with his beloved younger brother. Itachi feared losing Sasuke and the subsequent loneliness and sorrow that would follow if they became enemies. Their brotherly bond meant everything to Itachi.

3. Madara Uchiha: Initially mistaking him for Madara Uchiha, Itachi regarded the masked man with caution.

Seeking his assistance during the Uchiha clan massacre, Itachi took precautions by implanting Amaterasu in Sasuke's eyes, anticipating a confrontation with Madara. Recognizing Madara's formidable power, Itachi considered him a formidable adversary.

4. Hiruzen Sarutobi: The esteemed Third Hokage, Hiruzen Sarutobi, commanded the respect and admiration of the entire village. Entrusting Itachi with the grim task of annihilating the Uchiha clan, Hiruzen had taken Sasuke under his wing, making it difficult for Itachi to face him in battle. Itachi held immense trust in the Third Hokage.

5. Fugaku Uchiha: Fugaku Uchiha, the Uchiha clan's leader, and Itachi's father, possessed the Mangekyou Sharingan and potentially the ultimate dojutsu, Susanoo. Itachi held a deep respect for his father and feared confronting him, as he believed Fugaku could overpower him and demand he address him as "father."