The former striker, now 54, grew up supporting the Tannadice side and scored a Scottish Cup winner to break a long hoodoo. Brewster could not contribute in any meaningful way to ending Hibs' own Scottish Cup hex in the one season he had at the club in 2001/02. They were dumped out of the tournament in the fourth round by Rangers.
Brewster did score a couple of goals against Raith Rovers in a League Cup win and took part in a memorable UEFA Cup tie against AEK Athens, opposition he knew well.
He returned home after a successful spell in Greece to start a remarkable second act in Scottish football at the age of 34. Brewster was still playing in his early 40s but moved on more quickly than he would have liked from Easter Road.
“I had one year at Hibs when I came back from Greece in 2001,” Brewster recalled. “Big Alex [McLeish] invited me for a trial and I signed. Big Alex left for Rangers, and Franck Sauzee took over. I missed Franck’s era as manager because I was out after a shoulder operation, I think I played the last game.”
Sauzee's time in charge was more of a mini-era – he was sacked after 15 matches. Bobby Williamson took over.
“I finished the season strongly with Garry O’Connor,” continued Brewster, who is now based in Sussex, where he runs his own football academy and is development coordinator at Horsham FC. “I was confident I would get another contract, but Sky pulled out of Scottish football. Rod Petrie went: ‘Well, I am not signing any player until I know what is happening’.
“I went from a high to thinking ‘OK, what’s going to happen now?’ Jimmy Calderwood came in and offered me a two-year contract at 35 so I was one of those fortunate players at the time. I had just under two-and-a-half-years at Dunfermline.
“I really enjoyed my time at Hibs. It is nice to see them do well. But I think everyone knows where my priorities lie on Saturday…”
How could it be otherwise? Brewster’s winning goal against Rangers at Hampden in 1994 changed his life. “Well, having stood on the terraces five times watching your team and going home disappointed and suddenly finding yourself in a cup final and scoring the winning goal to beat Rangers…” he recalled. “If you look back, the Rangers team that day was full of internationals. They were going for the double treble. We were so far underdogs it was not true.
"But on our day that season we were really good. We had already gone to Ibrox and beat them 3-0 - it was 3-0 after 19 minutes. Ivan (Golac) made sure we believed. I think the performance from every player, from Guido [van de Kamp] right to Christian [Dailly], Andy [McLaren] and myself up front, everyone played to the maximum.
“That’s what has to happen to win tournaments," he added. "You need everyone pulling and your big players to come up with the goods.”