History now, though, appears to be weighing very heavily indeed upon the 23-year-old as he prepares for Saturday's meeting with Dundee United at Celtic Park.
Hasselbaink may not come across as the archetypal student of the game with his oversized baseball cap and trackie trousers, but he is all talk these days about the oldest trophy in world football and rewriting the record books.
There is no question he has grown to appreciate just how much it means to the Perth club to have reached their first Scottish Cup final and what joy it would bring to see truly meaningful silverware returned to the Fair City for the first time.
Within his ruminations, though, there was just the slightest suggestion that Hasselbaink's new-found fascination with the old tournament relates to a missed opportunity with his former club St Mirren and a chance to gain a degree of bragging rights over his old friends in Paisley.
"I left St Mirren and they won the League Cup, but it wasn't the Scottish Cup, eh?" quipped the Dutch striker. "The Scottish Cup is the greatest cup.
"You do wonder if your chance of winning a trophy has gone, but St Mirren did well last year to win a cup and I hope I'll have a chance to win one this year. My nerves are very high at the moment. The oldest cup in the world is there to be won.
"It is my first cup final since I played youth football and it is the first cup final for the club and most of the players. When I joined, I didn't realise the club had never won a major trophy. I didn't even realise that they were in the old First Division not so long ago, but we know exactly what is at stake now."
Recent events are also at the forefront of Hasselbaink's mind, though, as he looks for positive portents ahead of the biggest game of his life.
Just last month, PEC Zwolle upset the odds to beat Ajax 5-1 in the final of the Dutch Cup and win the first trophy of their 103-year history.
The game was held up for 30 minutes because of fireworks being thrown at the players and resulted in Ajax director Edwin van der Sar taking to the field to appeal for calm.
Hasselbaink expects Saturday to be a little less incendiary, but he sees the unlikely story of Zwolle as reason to believe that anything is possible.
"Zwolle were in the First Division in 2012, so it was a fairytale for them," he stated. "They will be in Europe for the first time too. Every small team tries to get to Europe through winning the cup and Zwolle showed what can happen."
Hasselbaink believes the way his side performed in Europa League qualifying, beating Rosenborg over two legs, should reduce the risk of stage fright at Celtic Park.
"I don't think we'll freeze," he said. "The Europa League was a new thing for many of us at the start of this season and we handled it well.
"We have built up our confidence over the season because we have done so well; no-one will be stressed on the day. I would prefer to play at Hampden because I have been here for four years and haven't played there. I've only been there to watch St Mirren's semi-final against Hibs. The pitch is always good at Celtic Park, though, and you can get more people in there than Hampden, so that is a bonus."