I’ve always had a bit of a fascination with the Scottish Highlands — maybe it’s the endless hills, the sense of isolation, or perhaps it’s just the sheer madness of running a football club hundreds of miles from anywhere. Those long journeys to away games, the hardy handful of fans who make the trip, and the eternal optimism of men in woolly hats watching a team that’s probably just drawn 0–0 again… there’s something beautifully tragic about it.

In Championship Manager 97/98, the most northerly of these brave souls to grace the Scottish Football League were Ross County — proud representatives of Dingwall, a town that could generously be described as “remote”.

At this point in history, Ross County were the new kids on the block, having only joined the Scottish Football League in 1994, joining the newly expanded Third Division. The club’s chairman was Roy MacGregor, the local businessman whose ambition would eventually propel County all the way to the Scottish Premiership. In 1997/98, the man in the dugout was Neale Cooper, the former Aberdeen midfielder and one of Alex Ferguson’s trusted lieutenants from the glory days at Pittodrie.

The challenge is simple enough: to outperform the real-life Ross County as they began their long, slow march towards Scotland’s top table.

But before that, let’s remind ourselves how they actually fared in real life under Cooper’s watch.

Season	Division	Final Position	Notes
1997–98	Scottish Third Division (4th tier)	3rd	Strong debut season under Cooper
1998–99	Scottish Third Division	1st – Champions	Promoted to Second Division
1999–2000	Scottish Second Division (3rd tier)	3rd	Consolidated after promotion
2000–01	Scottish First Division (2nd tier)	6th	First season at this level
2001–02	Scottish First Division	4th	Solid mid-table finish

And, because no challenge is complete without an arbitrary and completely unnecessary twist, I’ll be making things a little harder: every matchday squad must include at least one player named “Ross” — first name or surname. Because if you can’t fill your team with Rosses when managing Ross County, what’s even the point?

Apologies in advance for the upcoming state of the screenshots. I promise they looked perfectly crisp when I took them — before the train decided to wobble like a drunken centre-half at a corner. The quality will improve in future instalments, assuming my photography skills do too. First look at the squad — and, honestly, it’s not bad for a Scottish Third Division outfit. A good mix of journeymen, youngsters, and lads whose stats make you squint a bit and mutter “he might come good…” under your breath.

The club’s finances, however, are slightly less encouraging. A grand total of £86,000 in the bank and already £14,000 down for the month. The board haven’t said the word “austerity”, but it’s clearly the vibe. The plan, therefore, is simple: raid the free-transfer market, then flog a few squad fillers to keep the lights on.

Fortunately, the “Ross rule” practically enforces itself straight away — there’s already a Ross in the squad: veteran defender Ross Ruickbie, a solid old pro with positioning like a chess grandmaster and pace like a wardrobe. He’s 33, but he’ll do for now.

Here is real life Ruickbie in later years performing at the Highland Games. A man to build a team around!

Key men? Defensively we’ve got Mark Haro — a tackling machine and, despite what his surname might suggest, not a character from a kung-fu film. Further upfield, Gordon Connelly leads the line — a proper old-school Scottish striker, the sort who probably eats nails for breakfast and considers shin pads “optional”. Here he is bursting forward while his hairline stays further back in protest.

The first test comes quickly: Inverness Caledonian Thistle away in the Coca-Cola Cup. A Highland derby — just 14 miles separate the sides.

Before the big day, there’s transfer business to be done. I’ve gone full-on traditional CM2 recruitment mode:

• Andrew Duncan, Andrew Mainwaring, and Jason Crowe — all trusted free-transfer gems.
• Trevor Steven, veteran of Rangers and Everton fame, drafted in to add a touch of class (and hopefully not collapse from exhaustion).
• Wayne Carlisle, a young right-back with a name that sounds like a motorway service station.
• And, crucially, a backup Ross — goalkeeper Ross Bellotti, because you never know when disaster (or injury) will strike.

Carlisle and Steven go straight into the starting XI, with Mainwaring and Duncan on the bench. Broddle’s on corners, Connelly’s on shooting duties, and Trevor Steven takes the captain’s armband — because if you’ve got 36 England caps, you’re not letting Derek Adams boss you around in the dressing room.

And then — boom. Straight into giant-killing mode. Inverness, frustrated and outplayed, resort to two-footed challenges and end up with two men sent off. We stroll to a 2–0 win, with Connelly and Adams on the scoresheet. Not bad for a club that’s technically still unpacking its kitbags.

Maybe, just maybe, this Highland experiment won’t end in tears after all…

I decide to break the bank — if you can call spending nearly half my total funds “breaking” anything — with a £45,000 move for Liverpool and Ireland U21 prodigy Sean Friars. He’s just 18, fast, skillful, and has stats that make my existing midfielders look like they’re kicking with both feet tied together. If this goes wrong, we’re financially sunk, but at least we’ll go down stylishly.

First up in the league: Arbroath at home. They’re dancing in the Moonlight (that’s genuinely the scorer’s name — not a poetic metaphor), but two late goals from Mainwaring and Connelly ruin their evening and send them on the long, 155-mile trek back to Gayfield Park in silence. 2–1 to the Staggies, and the Ross County express keeps rolling.

Next, it’s back to cup action against top-flight Kilmarnock. After the Inverness scalp, confidence is high — could we pull off another giant-killing?

The answer is a resounding no. Despite dominating possession and peppering their goal with shots, Killie clinically slot three past us without breaking a sweat. Welcome to reality, population: me.

To make matters worse, Mark Haro, my best defender and the spiritual leader of the backline, goes down with a hip injury — out for four months. Hardly the rugged Highland warrior I’d imagined. The door creaks open for youngster Andrew Duncan, whether he’s ready or not.

No time to mope — League Challenge Cup next, and it’s Division 1 side Hamilton Academical visiting Victoria Park. The lads rise to the occasion, Richard Hart bagging both goals in a 2–1 win. Another “giant” slain.

Back to the grindstone in the league — a 204-mile trek to Berwick, practically the other end of the country. We take an early lead, but disaster strikes: Ross Ruickbie, our namesake talisman, sees red after just 19 minutes. Down to ten men, we dig deep and somehow hang on for a 3–2 win. Spirited. Nerve-shredding. Utterly unsustainable.

With Ross suspended, I decide to blood Ross 2 — young keeper Ross Bellotti — for the next trip, away at Montrose. It’s a chance for the lad to shine.
It does not go to plan.
Despite Montrose being reduced to ten men after just eight minutes, they absolutely dismantle us 6–3. Bellotti is injured early, Mainwaring ends up in goal, and concedes approximately every time the ball crosses the halfway line. We officially have a Ross crisis.

Something’s got to give. With one Ross crocked and the other suspended, I need a Ross 3 to keep the sacred name alive. Sacrifices must be made.
Sorry, Paul Bradshaw — you’re released on a free to make space for the next man in the Ross dynasty. IRL Bradshaw made just six appearances for County, before disappearing from Football.

The “Ross situation” continues to dominate early-season life at Victoria Park. Ruickbie isn’t suspended just yet, and he even chips in as we somehow conspire to throw away a 2–1 lead and draw 2–2 with Queen’s Park.

But when Ruickbie’s suspension finally hits, and Bellotti remains sidelined, the hunt for a third Ross becomes desperate. After scouring every corner of the Scottish lower leagues (and most of northern England), we uncover a candidate: Ross Taylor, a right-back so unremarkable that the scouting report simply read “available”. Still, rules are rules — welcome to the madhouse, Ross 3.

Taylor makes his debut just in time for our next away trip — Alloa Athletic, roughly 150 miles south of Dingwall. It’s our first proper stinker. We lose 3–0, look like we’ve never met each other before, and even Sean Friars — my £45k wonderkid — plays like he’s allergic to footballs.

Back home, though, we’re straight back into cup mode. Division Two’s Brechin City visit Victoria Park in the League Challenge Cup, and more than 2,000 fans turn up — proof that the people of Dingwall love a cup tie, or possibly just love the idea of central heating on a Thursday night.
It’s a thriller: Friars and Wood score late to take it to penalties. We hold our nerve… until Furphy, my deep-lying “playmaker” (quotation marks doing heavy lifting there), misses the very first kick. We go out 5–4. Of course we do.

Back to league action and some joy. East Stirling rock up and are promptly dismantled 4–0. Mainwaring, Connelly, and yes — Ross Ruickbie himself — all on target. Order, briefly, restored.

After six league games, it’s time to take stock. We’ve battled suspensions, injuries, and a revolving door of Rosses, but somehow, we’re sitting 4th in the table, just one place shy of the required spot to match real-life 97/98 County and prolong the challenge. It’s respectable — but this is only the beginning.

Next time:
Can we mount a real challenge?
Will Friars justify his price tag?
And will any of the Rosses survive an entire month uninjured, unsuspended, or un-sacked? Find out in Part Two: The Ross Revolution — coming soon to a slightly steadier train carriage near you.