Italy, both world wars if you count that
this post was submitted on 27 Feb 2025
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The Sino-Soviet split is similar. Neither was the other's "master," but relations deteriorated.
Though the split happened because the Soviets thought they should be master of all Communist countries and the Chinese had different ideas on the topic.
It's a lot more complicated and messy than that, and for what it's worth they nearly repaired relations before the USSR dissolved.
Italy, twice, on both world wars.
If we take "old allies" not so much as old friends but more as "previously allied with:" Japan was on the side of the allies in WW1 but was axis in round 2. Nazi-Germany invaded the USSR in spite of their peace pact. Napoleon and tsar Alexander of Russia were on somewhat friendly terms before Alex clandestinely rejoined the coalition against the French.