As Munster's elite player development officer, and the assistant coach of Ireland's under-20 squad, the former Scotland scrum-half and proud Borderer marvelled at the way his new charges inflicted a terrific defeat on their South African hosts at the Junior World Championship.
Then he winced at the sight of the Scottish youngsters being pummelled 67-12 by Australia in the same competition. And finally he rejoiced when Greig Laidlaw kicked the last-ditch penalty which brought the senior Scots their first victory over Australia Down Under for 30 years. Starkly contrasting results in different continents; the only constant was the rain.
Oliver has been involved in some grand occasions, as player and coach, and despite having won only three Scotland caps, his instinctive feel for the game and ability to unearth and nurture precocious talent has earned him plaudits wherever he has ventured.
He left his homeland five years ago to become director of rugby at Garryowen – his wife is from Limerick and his father-in-law has strong connections with the Irish club side – and hasn't looked back in the intervening period, whether excelling with Munster, or in his present dual role.
As he kept tabs on what was unfolding in the sport last week, Oliver could have been forgiven for feeling disorientated: here he was in the Cape, working in tandem with Mike Ruddock, the Welshman who tasted grand-slam success, while Ireland, Wales and England prepared to tackle New Zealand, Australia and South Africa this weekend across the Southern Hemisphere.
As befitting his perfectionist streak, Oliver is dedicated to watching every second of the action, and has backed the Northern Hemisphere teams to create similar headlines to those that greeted Scotland's unexpected triumph.
"It was fantastic to see the Scots' performance [in Newcastle]; they were heroic, they stuck to their task, made a huge number of tackles, and several of their youngsters, such as Stuart Hogg, Tom Brown and Matt Scott, showed the progress they have made. I was delighted for Greig, because I have always had a high regard for him; he has a great rugby brain," said Oliver, who has previously offered advice and encouragement to the Edinburgh half-back.
"The Scots had been on the receiving end of some narrow defeats, at the World Cup and the Six Nations, but it looked as if they had toughened up from those experiences and the manner in which they seized the moment, when the match was balanced on a knife edge, was very impressive.
"The other home nations will have to display the same qualities, but I think the Welsh could put fresh pressure on Australia, as they have come on in leaps and bounds in recent months. They are in a good place. Their confidence is sky high since they won the grand slam, their coaches and management have instilled a fresh mentality where the players realise what happens off the pitch matters as much as on it, and they have a terrific group of young players who can cause Australia problems.
"It will be harder for the Irish against New Zealand, who have such a fantastic record in Auckland. Ireland, rather like Munster, are in transition, because they are a side which has grown old together. On the other hand, as was obvious in the RaboDirect PRO12 and the Heineken Cup, there are outstanding talents ready to grab their chance in Ireland, and this could be the dawn of a new era. They couldn't have asked for a sterner challenge, but these tours are all about learning quickly.
"As for South Africa against England, that is too close to call; there is loads of hype over here about how the Springboks have a new coach and captain, and plenty of new blood in their ranks, and England are in a similar position, so it's a step into the unknown. But Stuart Lancaster did well in the Six Nations and England always pose a threat."
In the prelude to these Tests, Oliver's army will be maintaining their Under-20 charge. It is hard not to wonder how the Irish ingenues could overcome South African opponents who boasted five players with Super 15 experience, while the Scots were blown away by the physicality, pace and power of their Australian rivals.
Typically, Oliver refused to admit there was a massive gulf between the countries. Instead, he insisted, the crux lies in Scotland performing to their true potential.
"You have to sort out your systems and play to your strengths," he said. "The Scotland under-21s almost beat the Aussies a few years ago, so the gap isn't insurmountable but if you miss tackles against any opponents the chances are you will struggle. From what I've heard, the [Scottish] Academy sides are making progress, and you can see, in the emergence of Hoggy, Matty [Scott], Tom [Brown] and others, that there is plenty of young talent in Scotland.
"It's about how these lads are managed; if they are given regular games, they will develop consistency and confidence. I watched Hoggy against Munster and he was outstanding; he benefited from being flung in at the deep end [by Scotland when Rory Lamont was injured], so perhaps there's a lesson there."
You listens to Oliver and wonder why he isn't coaching in his homeland. Then again, Scottish sport is littered with coaching success stories achieved in foreign climes.