It can help if we keep in mind when something is said, as well as the state of knowledge (about the game result) at the time of the expressed expectation. For example:
All the sentences below occur on January 7th:
(Minha expectativa antes do jogo, resultado necessariamente desconhecido)
On January 1, I had expected Tom would win the game taking place on January 5th. (a melhor expressão)
On January 1, I expected Tom to win the game... (inferior, mas plausível))
(Minha expectativa após o jogo, sem saber o resultado)
On January 6, still not knowing the result of the game, I still expected Tom to have won the game that had taken place the previous day, January 5th. (melhor)
Impossivel usar "to win" neste caso, para um evento já no passado.
(Minha expectativa após o jogo, resultado conhecido)
Today, January 7th, now knowing the game result, I can say I had expected Tom to have won the game that took place on January 5th.
Possivel usar "to win" neste caso, mas "had expected" é necessário.