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Chronologically:
Spiral Labyrinth (Side Stories / Gaiden 2, episodes 1-14)
Valley of White Silver (Side Stories / Gaiden 1, episodes 1-4)
Those Who Revolt / Mutineer (SS / G2, ep. 15-18)
Those Who Duel / Duelist (SS / G2, ep. 19-22)
Golden Wings
Those Who Recapture / Survivors (SS / G2, ep. 23-26)
Morning's Dream, Night's Song (SS / G1, ep. 5-8)
A Hundred Billion Stars, A Hundred Billion Lights (SS / G1, ep. 13-24)
The Third Tiamat Battle (SS / G2, ep. 27-28)
My Conquest is the Sea of Stars
Disgrace (SS / G1, ep. 9-12)
Overture to a New War (an expanded retelling of the first two episodes of the main OVA series)
Main OVA series
G1 = A Hundred Billion Stars, A Hundred Billion Lights Gaiden
G2 = Spiral Labyrinth Gaiden
Release Order:
My Conquest Is the Sea of Stars (Film, 1988)
Legend of Galactic Heroes, Season 1 and 2 (OVA series, 1988–1992)
Golden Wings (Film, 1992)
Overture to a New War (Film, 1993)
Legend of Galactic Heroes, Seasson 3 and 4 (OVA series, 1994–1997)
Legend of Galactic Heroes Gaiden (OVA side series, 1998–2000)