Kabuto vs Gaara

Round 1: Kabuto (Chunin Exams arc) vs Gaara (Chunin Exams arc)

Restrictions: Shukaku transformation and Summonings

Knowledge: Full

Location: Chunin Exams arena

Round 2: Kabuto (Sasuke Retrieval arc) vs Gaara (Sasuke Retrieval arc)

Restrictions: Shukaku transformation, and Summonings

Knowledge: Full

Location: Where Gaara fought Kimimaro

Round 3: Kabuto (Beginning of Shippuden) vs Gaara (Beginning of Shippuden)

Restrictions: Shukaku transformation and Summonings

Knowledge: Full

Location: Where Gaara fought Kimimaro

Round 4: Kabuto (War arc) vs Gaara (War arc)

Restrictions: Edo Tensei and/or Summonings

Knowledge: Full

Location: Where Gaara fought Kimimaro

Gaara all.

Kabuto wins the last round if he starts with sensory attacks.

Round 1: Kabuto easy, he proved more than once he was high Jonin level. He even contended with Kakashi for a bit, was stated to be on his level, and was able to dodge Tsunade.

Round 2: Gaara should actually win this one, Kabuto isn't living the sand tsunami imo.

Round 3: Gaara stomps here in my opinion.

Round 4: Kabuto, sage mode in general is a massive amp.

Kabuto takes R4 and R1. Gaara takes R2 and R3.

Gaara wins 2 and 3 but loses rounds 1 and 4.

Kabuto is as fast as kakashi, he juggles gaara for the first 2 rounds.

Early shipuden gaara should stomp kabuto.

War arc: too close to call. I'm leaning kabuto though due to genjutsu

Kabuto all rounds except round 3, and maybe round 2.

People are underestimating him. He was stated to be Kakashi tier, made Tsunade bleed, was Orochimaru’s number 2, meaning he was likely above Kimimaru who only lost to Gaata because he was sick, and as sage mode he was fighting Sasuke and Itachi at the same time, and each one of them is above Shippuden Gaara.

Kabuto round 1 easily he was compared to kakashi and back then jonin spanked the kids.

Round 2 gaara wins easily with shukaku kabuto gets stomped

Round 3 gaara wins easily he can overwhelm kabuto with sand no problem

Round 4 Kabuto is medium difficulty only because hes overconfident. With sage mode hes can use brachen dance to own gaara like before and he has tayuya genjutsu which is GG then muki tensai which is GG