Sith Vs Jedi/ team vs team

I decided to take Jedi and Sith from all eras to make this more interesting

Ancient era 

Tau and Karness Muur (when he is was alive, so no feats/statements regarding Muur after this are allowed)

Start of Old Republic era


Naga Sadow (Prime) and Odan Urr (prime)

Mid Old Republic era


Exar Kun (pre ritual) and Jedi Revan (i believe he is also known as redeemed Revan)

End of Old Republic


Satele Shan and Darth Marr (both are in prime)

PT era (also known as New Republic era)


Obi Wan Kenobi (ROTS) and Darth Maul (SOD)

Original Trilogy era (post jedi purge)


Sedriss and Starkiller (both in prime)


New Jedi Order


Luke Skywalker (DE) and Kyp Durron (dark sider, under Exar Kun's influence)


Late New Jedi Order


Kyp Durron vs Darth Caedsu (both are in prime)

Legacy era 


Cade Skywalker (prime, no dark side allowed) and Asharrad Hett (before he became Krayt)

Tau Idair, Odan Urr, Jedi Revan, Satele Shan, Obi-Wan Kenobi, Starkiller, Luke Skywalker, Kyp Durron, Cade Skywalker vs Karness Muur, Exar Kun, Darth Marr, Darth Maul, Sedriss, Kyp Durron, Darth Caedus, A'sharad Hett





If it goes as you've arranged it:

Karness beats Tau by virtue of having shaky parity with 19 BBY Vader, who would stomp Tau. 

Naga Sadow beats Odan Urr.

Exar Kun beats Jedi Revan.

Marr slaughters KOTFE/KOTET Satele in sabers and narrowly wins in Force.

Obi-Wan beats Maul in a close fight.

Starkiller hands Sedriss his arse on a platter.

Luke beats Kyp.

Caedus beats Kyp due to vastly superior lightsaber skill as well as better Force mastery and versatility/hax.

Cade might beat A'Sharad, not sure. A'Sharad is a much better duelist but probably weaker in the Force.


So, the final score is 5 for the Sith, 3 for the Jedi, and one inconclusive one. 

The Sith win.

Alternatively, if it's a proper fight and not individual rounds then SK helps Kenobi beat Maul faster then the duo help their teammates. SK would help Tau while Obi-Wan helps Revan against Kun. They turn the tide in those fights, and help the rest of their team to victory.

Tau vs Muur

Naga Sadow vs Odan Urr

Exar Kun vs Revan (if this is pre Kotor jedi Revan)

Marr vs Satele

Obi Wan vs Maul

Sedriss vs Starkiller

Luke vs Kyp

Caedus vs Kyp

Cade vs Hett