Such was the impact he was making in the top flight with Kilmarnock, the Northern Ireland internationalist found himself on the shortlist for the Players' Player of the Year award last season following a successful season at the Rugby Park club including lifting the Scottish Communities League Cup in March.
With his contract expiring with the Ayrshire club, there was no shortage of interest in the 27-year-old from England and beyond. Shiels even flew across the continent to discuss the possibility of trying his luck abroad during the summer.
In the end, however, the lure of Rangers proved too much. The Ibrox club may well have been starting out all over again in the Irn-Bru Third Division, but the opportunity to play in front of a massive support in almost every home game, and also command a wage most SPL clubs could not come close to matching, was enough to see him sign for the Light Blues.
Big things, of course, were expected of Shiels, who has already netted six times for Gers this term. Although he hasn't quite managed to deliver quality performances as regularly as boss Ally McCoist would have liked – like many of his team-mates – there have been flashes of magic from Shiels in recent weeks.
On Sunday, he netted a sublime opener away to Clyde to send his side on the road to a 2-0 victory and, in the previous match, he put the opening goal on a plate for Lee McCulloch against Queen's Park with a solo run.
Having scored five times for Kilmarnock against Inverness Caley Thistle last season, Shiels will relish the chance of lining up against the Highlanders again.
And former Rangers striker Kevin Drinkell has no doubt that a touch of Shiels magic could make the difference in tonight's League Cup quarter-final at Ibrox.
He said: "I think Dean does have that spark in him that can make a difference. Not only does he score some great goals, as we saw against Clyde on Sunday, he is also capable of creating things for others like he did for Lee McCulloch against Queen's Park the other week.
"So, Dean has it all in his locker, and I will be surprised if he does not go on and score a barrow load for Rangers this term. The great thing for him is that he is enjoying, or should enjoy, more of the ball than he has done in previous seasons with the likes of Kilmarnock.
"In the Third Division, the club should become increasingly dominant and that will mean Dean will feature more prominently and, in turn, that should give him even more confidence to express himself.
"So he is coming into what is a very important game on the back of a good performance and an excellent goal.
"I think Dean had a fair bit of success against Inverness last season for Kilmarnock [five goals in four games], so he will be relishing the chance to test himself against them again."
Tonight's 7.45pm kick-off will also provide an opportunity for the likes of Lee Wallace and Ian Black to re-post their case for Scotland inclusion.
The former Ibrox hitman said: "I think the game takes on extra significance for these two in terms of pushing themselves for their country.
"What they do against Third Division sides is largely irrelevant when it comes to playing for Scotland so, when they do meet SPL opposition in the cups, they have to make the most of that opportunity."
When it comes to selecting a winner tonight from the two sides managed by his former Gers team-mates, McCoist and Terry Butcher, Drinks believes an away win could be on the cards.
He said: "I think it will be very tight tonight, but I also believe Terry Butcher will have Inverness wound up to come and have a go maybe more than normal.
"In that respect, it is likely to be an open game as Rangers will be determined to prove their win over Motherwell was not a one-off.
"But Inverness are on a decent unbeaten run and all the new players Terry has brought in have gelled, so this will be a real test."
When it comes to Gers travails in the basement, Drinkell admits he has been surprised by how hard the Ibrox side are finding life in the bottom tier of the Scottish game.
He said: "I think the thing that surprises me is how many times Rangers have failed to learn their lesson on the road. They were lucky to get away with a point at Peterhead, then again at Berwick, and also Annan, but still did not learn.
"Then they lose at Stirling and I found it surprising it has taken them five games to get their first win away from Ibrox. Hopefully, they have now turned the corner."