The winger made a breakthrough during the 2003/04 season, finishing the campaign with the only goal in a 1-0 win at Ibrox. He became a key member of the squad the following year, playing in big European nights against Basel and Braga.
When things began to change at Tynecastle in the summer of 2005, he followed Craig Levein and former Hearts team-mates to Leicester City.
Nearly 16 years later and Hamill is still playing.
In a recent friendly against Tollcross Thistle, he was dictating play in the middle of the park for Haddington Athletic. In addition, he is also manager of the East Lothian club who play in the East of Scotland Football League 1st Division Conference A, step seven on the pyramid.
A position he has held for nearly four years.
But it wasn’t the one he originally planned for having followed David McGlynn to the Hi-Hi’s from Bonnyrigg Rose via Linlithgow Rose in search of coaching experience under the well-known junior football manager.
It wasn’t until a surprise exit for McGlynn presented Hamill with the chance to really get his teeth into coaching.
"The committee had a meeting, spoke to me and asked if I would like the chance to manage the team. I didn’t hesitate.
“I’m loving it. What makes it a lot easier are the players.
"When you’ve got the committee behind you, the coaching staff that you’ve worked with [Scott Bonar and David Simmonds], it just makes your life easier and you enjoy it.
"So far it’s been a pleasure.”
Sticking to his word
Of the 11 players who started for Hearts that evening in Basel, it is only Hamill and current boss Robbie Neilson operating as a head coach.
Hamill has sought some influence from his former coach John McGlynn someone he calls “one of the good guys”, but it is not a regular occurrence.
A self-confessed “journeyman”, he has taken his own path in management, using his own experiences as a player to shape how he is as a boss.
"There were a few managers I worked under where I said I’d never do that with the players if I became a coach," Hamill said. “And I’ve stuck to my word.
"I think the management style has moved on from old school. We don’t say much from the side. We don’t scream and shout.
"Everybody’s different, players react differently but we just feel a word with them at half-time, a word with them on a Tuesday after a game rather than screaming and shouting at them on the pitch.
"Players know when they’ve made a mistake or had a bad game so why do you need to be right down their throat and maybe put them in their shell more.
“We try to encourage them and get them out the wee rut they’re having.
"I’ve been there as well. Sometimes you just don’t want the ball anymore, you just want to hide.”
Across his four years as head coach he has built a young, talented team designed to play positive, patient football, going against a more simple and, what could be perceived by some at that level, effective approach.
It has been one of Hamill’s key challenges. To get those above him to buy into the vision, while building a side who can play it.
“The way we want to play football, it is not back to front stuff, it’s about patience, keeping the ball, movement," he said.
“We want to keep the ball more, get our patterns going. They’ve done it, the players have bought into it. There will be bad times but everyone needs to stick together.”
It is working.
Haddington are on an upward path under Hamill, Bonar and Simmonds.
Before the league campaign ended early, the Hi-Hi’s sat unbeaten in second. And they made waves in the club's first ever foray into the Scottish Cup.
Until Brora defeated Hearts, Haddington's 3-2 victory over Lowland League BSC Glasgow may well have been the shock of the tournament.
Hamill had to watch on from the small club house in the narrow home defeat to Formartine United in the next round due to suspension.
“That’s memories,” he said. “We were getting changed in a gym hall. It will live with the players forever. It was unreal.
"Moments like that, everyone’s together, everyone’s in it. The effort from everybody was tremendous.
“BSC were a very, very good side. It was meant to be, just amazing.
“It’s financially rewarding as well.
"We have got a couple of main sponsors. We rely on lottery money, going about pubs and trying to get people to sponsor us so any money for the club is brilliant.”
Hamill, who is still going through the different coaching badges, is not short of ambition for himself and the club. He wants to manage in the SPFL. But he also wants to take Haddington there.
If he was to lead the Hi-Hi’s, who play in a rugby town, to three promotions it would be a feat which would rival any other in domestic football in Scotland.
“We’ve got a plan, where we want to go and that’s why we have got younger kids who have ability and want to learn," he said.
"If we stick with it we’re confident we can do something with the team, take it up leagues.
"I know it’s pie in the sky stuff some people may think. Why can’t we?
"The committee, the effort people have put in to get this club where it is, it’s incredible.
"The amount of new houses getting built in the town, we are trying to create a huge family community club.
"That’s the aim but if you’ve not got that and you are just happy where you are then what’s the point being a player or coach if you are not wanting to better yourself.
"We’ve got potential.”