I think mostly not, for two main reasons.
First, Ollivander implies if he had known what Voldemort's yew wand was going to do (i.e. murders, dark magic, create The Boy Who Lived) he might have done something differently (he doesn't specify what).
Mr Ollivander touched the lightning scar on Harry’s forehead with a long, white finger.
‘I’m sorry to say I sold the wand that did it,’ he said softly. ‘Thirteen and a half inches. Yew. Powerful wand, very powerful, and in the wrong hands ... Well, if I’d known what that wand was
going out into the world to do ...’
Philosopher's Stone - page 64 - Bloomsbury - chapter 5, Diagon Alley
Dumbledore himself admits when he first met Voldemort he did not suspect that eleven-year-old Tom Riddle would go on to become the most dangerous dark wizard in history, although he found Tom Riddle odd and entitled, and enough of a gut feeling to keep a close eye on Tom while he was a student at Hogwarts. If Dumbledore couldn't put his finger on exactly what would happen between Tom Riddle/Voldemort and Harry Potter at the time(s) that the twin core wands were created (which canon doesn't address), I don't expect Ollivander would have been able to.
The second and more important reason, I think, is that there was absolutely no connection between Harry and Voldemort until Voldemort took stock in Sybill Trelawney's prophecy and marked Harry as his equal. The prophecy is only authoritative because Voldemort chooses to make it so. He continues to do so throughout the series because he doesn't know the whole prophecy, as Snape, while spying on Dumbledore and Trewlawney as a Death Eater, only overheard part of it and misreported the prophecy's predictions to Voldemort.
If I recall correctly, the only individuals who knew what the full prophecy said by the time we get to Half-Blood Prince are Dumbledore and Harry. Later, Harry tells Ron and Hermione about the prophecy, at Dumbledore's prompting (Half-Blood Prince - chapter 4 - Horace Slughorn) .
This happened after at least one of the Phoenix feather wands had been made -- Voldemort's yew wand. Tom Riddle was a first year at Hogwarts around 1936-1937. Harry wasn't born until 1980. And we have no idea when Harry's wand was actually made. So, I err on the side of Ollivander not knowing exactly what might happen between Voldemort's and Harry's wands.
That said, undoubtedly Ollivander, arguably the most skilled and intuitive wandmaker in the Wizarding world, would know that wands with twin cores are capable of Priori Incantatem. So, Ollivander remembering every wand he's ever sold, might have been able to know at the moment both wands were made and in existence, that if they met in a duel, Priori Incantatem would be possible. Ollivander knew that Voldemort had the yew wand and that Harry had the holly wand, and he knew about the twin cores, so it's clear he would have been able to know about the possibility (however remote) of Priori Incantatem, which did indeed occur between Harry and Voldemort in Goblet of Fire.