The first of those were in despair down in Tasmania, when the midfielder dislocated his shoulder in a pre-season match only weeks after returning from surgery.
It pushed his timeline back again, meaning he didn’t play until Round 13 and faced another road of recovery.
But as time would tell, his next batch of tears would be imbued with joy, coming in the middle of the MCG after he’d won his first premiership on the last day in September.
“I was on the bench in the last 30 seconds, and I started to get emotional once Checkers took a mark and kicked it down the line I knew we were going to win,” Lipinski recalls.
“I could feel tears coming and then the siren went, and we just jumped up and down.
“I hugged Fly and then I ran on and I can’t even remember who I hugged honestly; I hugged pretty much everyone.
“Then suddenly my girlfriend Chloe was on the field and hugging me and I started crying again.”
It’s a reflection of the journey Lipinski has been on since arriving at the Club at the end of 2021.
Admittedly, as the man himself says, he walked into a team who had just placed second-last and was in the midst of finding a new coach.
But he quickly found his feet, as the did the team as a whole, with Lipinski averaging 21 disposals across his 39 games for the Club in the past two seasons.
“When I first arrived, you could almost say the Club was in a bit of turmoil, I think they’d just finished 17th and didn’t have a great year and I obviously decided to come to Collingwood and I’d basically decided before they’d even announced that Fly was coming, so I kind of took a stab in the dark,” Lipinski said.
“Once Fly came it was just a perfect match, he’s just the best coach and he’s driven the best culture ever and even to start the year in 2022 we were a bit up and down, but the culture was really good and then from about Round 10 to now we’ve barely lost.
“It’s the best feeling in the world, you really work your whole life to even get one game in the AFL and then you want to cement your spot and now to be a premiership player it’s the best feeling ever.”
Of course, Lipinski’s Grand Final week was a little different to most of his teammates, having been named the sub for the game.
While disappointed not to be in the starting 22, the 25-year-old knew it wasn’t the time to be upset, knowing he had to be ready at any moment.
“I think it was Thursday afternoon I was just walking back from a massage and got called in to go to Fly’s office so I kind of knew that I’m going to be sub,” he said.
“Basically, Fly just told me that I was going to be sub for the Grand Final and obviously everyone wants to be in the 22 but it’s not the right time to sulk, I was playing in a Grand Final in two days so I was still very grateful that at least I’m playing.
“I was just like ‘alright, I’ll accept that responsibility, I’ll try be the best sub I can be and be super positive about it’.
“We had the Grand Final parade the next day so I was like ‘let’s enjoy that and get ready to play’ so that was basically my mindset, I didn’t want to sulk about it or anything.”
In the end, Lipinski played a large majority of the game anyway after Nathan Murphy’s unfortunate concussion early in the contest.
Embracing each moment, Lipinski recorded 16 disposals in the four-point win and put his name down in the Collingwood history books.
“At quarter time I saw him stumbling around a bit so I thought I might be a chance to get on,” Lipinski remembered.
“It was selfless by him, he could’ve easily gone back and gone on the ground and tried to play but he knew that we had myself waiting there and I could be fresh, so Murph told me to be ready and I guess I was.
“It takes years and years of hard work for everyone, everyone has got their own story, everyone has gone through setbacks and adversity whether it’s injuries or form or having to move clubs, there’s probably 10 blokes that have moved clubs to play in this team.
“Most importantly it’s probably the little things every day just being a professional because it just accumulates.”