This is not an easy task, and forgive me if one or more of your favourite players have been omitted, but there are many cases where any number of names could have been chosen.
This week I will give you the first four teams, in alphabetical order, starting with Celtic.
Goalkeeper seems a straight choice between Peter Johnson and Clive Watt. I’d give the former the nod, based mainly on the number of Shetland caps he received, although Watt was probably unlucky in that he played at the same time as John Johnson and Bobby Wiseman.
The full backs are fairly easy – county stalwarts Geordie Hunter and Robbie Simpson. I can’t think of anyone better.
Shane Jamieson gets a place in central defence with Joel Bradley just pipping Robert Smith as his defensive partner.
Finn Watt, who has been impressive in recent seasons, is on the right further forward. Gordon Barron, a hugely underrated player who turned out for Celtic in the 1990s, fills the central position with Paul Regan completing a midfield trio.
Up front the choice is pretty straightforward – three players from three very different eras. Goal-scoring machine from the 1960s Jimmy Mouat is joined by Colin Grant and current trailblazer James Aitken.
Other Celtic representatives unfortunate to miss out include Ross Moncrieff, Peter Fraser, Tommy “Tiny” Jamieson and Tony Johnston.
Moving on to Delting, although the North Mainland outfit is the newest team of all the eight, a strong line-up can be mustered over the past 30-plus years.
The keeper has to be Craig Dinwoodie, who has no equals among his side’s other custodians.
County regulars Leighton Flaws and Peter Peterson get the full-back slots, with Merv Jamieson and Gerry Kearney in central defence. Joe Hunter is unlucky to miss out here.
There are no difficulties with the three midfield positions – Alan Duncan, David Clubb and Ross Jamieson are all virtually bolted on.
One of the strikers must be Stuart Hay while the other two are harder choices. I will go with Peter Keenan and Ross McDougall, although John Jamieson and Gary Sutherland are also worth consideration.
Moving on to Ness United, a few players could have been chosen for the other sides they represented during the times Ness were absent from senior participation. But I will go on the assumption they would have played for their home club had there been one.
Not surprisingly, Ness players from three eras make up the bulk of the line-up – the champion side of 1966, the team which pushed so hard for the title in 1995, and the current improving squad.
Brian Munro will go between the sticks, with Jim Budge and Erik Peterson the other names in the mix.
The one certainty in defence is centre half Ian Manson, who is literally head and shoulders above any other contenders. As his central partner I would be swayed towards Stuart Copland, with Sandy Peterson and Brian Manson in the full back positions.
Defenders who just miss out are Billy Adamson, Liam Flaws and Alistair Johnston.
Midfield is much less trouble – and it’s a Sandwick triumvirate. Kenny Malcolmson would be flanked by Jack Halcrow and Ewan Odie, although a fourth Sandwick man, Graeme Sutherland, comes close.
Up front there are a number of players in contention. So with apologies to Raymond Aitken, Malcolm Adamson and Dougie Bray, I would go for the latter’s son Duncan, Chris Donald and Lol Aitken. The last name may not be so familiar, but in his one match against Orkney he scored twice – in the famous 9-7 match of 1963.
Terry Johnson is the keeper – his athletic prowess was outstanding and his longevity impressive. Glenn Gilfillan was the only other contender. My back four would be Tommy Burgess, Ian Gray, Arthur Williamson and Charlie Johnson, although it disappoints me to leave Len Laurenson out.
Grant Gilfillan, Sydney Goodlad and Davie Atkinson would be in midfield, with Jim Leask, George Jamieson and David Johnson also in the running.
Up front I would go for Davie Leask, Bert Sinclair and Ernie Smith, although I guess Steven Umphray and John Pottinger are among the other serious claimants.
Scalloway were such a strong side that you could almost have named a second team, with others worthy of mention including Billy Garson, Frank Gilfillan, Oliver Henry, Dougie Dalziel, Ian MacDonald, Gordon Bolt and Ross Duncan.
Next week will be the turn of Spurs, Thistle, Whalsay and Whitedale. Remember, if you have any thoughts on this feel free to email me at firstname.lastname@example.org
GEORDIE HUNTER (captain)
DAVID CLUBB (captain)
IAN MANSON (captain)
SYDNEY GOODLAD (captain)