Ross County were forced to settle for two points against Buckie Thistle after winning the penalty shoot-out which followed their 1-1 draw at Victoria Park.
It was a far from comfortable afternoon for Malky Mackay’s men, who fell behind to Sam Urquhart’s goal early in the second half.
The Jags put themselves into an excellent position to claim a memorable victory, however their lead lasted just eight minutes before substitute Dominic Samuel levelled.
Although Scott Adams spurned a glorious chance to win it for Buckie, the sides could not be separated in 90 minutes.
It was the Staggies who claimed the shoot-out win, with Ross Callachan netting the decisive spot-kick in a 5-3 win.
Nevertheless it was a tricky start to the competitive season for the Dingwall men, who play their next Premier Sports Cup tie at home to Dunfermline next weekend.
County handed four of their new signings competitive debuts from the start, with Ben Purrington, Owura Edwards, Yan Dhanda and Jordy Hiwula selected.
There was also an outing for youngster Ross Munro in goals, with newly-signed Jake Eastwood on the bench.
Buckie, whose manager Graeme Stewart was serving the first match of a touchline ban, handed first outings to goalkeeper Balint Demus, Ryan Fyffe and Cohen Ramsay.
The Staggies nearly took the lead inside just 20 seconds, when Edwards teed up Ross Callachan for a low strike which was palmed wide by Demus.
Buckie settled into the game however, and succeeded in limiting clear openings for their Premiership opponents. Edwards looked to cause more problems down the right hand side on 16 minutes, with his menacing looking ball to the far post finding no takers.
A well-worked set-piece nearly led to a County opener on 28 minutes, when Callachan’s low free-kick was neatly flicked by Dhanda to set up Hiwula, however his drilled effort was touched to safety by the Jags defence.
Buckie had their first meaningful attempt a minute later, with Sam Pugh taking aim with a swerving shot from long range which was well read by Munro.
The Staggies continued to push for a breakthrough before the interval, with Ben Paton sending a low effort past the post, while on the stroke of half-time Hiwula was inches from getting on the end of an Edwards delivery when any contact would almost certainly have resulted in a goal.
It had been a frustrating opening 45 minutes for the Dingwall men, who looked to freshen up their attack at the break. Dominc Samuel and Josh Sims were brought on, with Dhanda and Jordan White making way.
Sims nearly made an immediate impact on 48 minutes, after getting on the end of a low Edwards cross but seeing his snapshot well matched by Demus.
It was the Jags who took a shock lead on 53 minutes. The Staggies defence made a mess of dealing with a Marcus Goodall delivery from the right, with Urquhart arriving to prod the ball beyond Munro into the far corner.
Buckie took a huge lift from breaking the deadlock against a stunned Staggies side, with Goodall close to adding a second when he met a Kevin Fraser cutback before unleashing a shot which drifted just wide.
County spurned a glorious chance to level just before the hour mark when Edwards played Hiwula clean through on goal, with the former Doncaster Rovers forward blasting his effort well over with only Demus to beat.
It could have been a costly miss but County did restore parity just moments later. Edwards was again the supplier with a tidy flick to play Samuel in, with the forward bearing down on Demus before applying a crisp finish in at the goalkeeper’s near post.
Buckie refused to be deflated by losing their lead, with the lively Barry sending a strike into the arms of Munro from the edge of the box.
County dominated the bulk of the latter stages in their search for a winner but Buckie had a glorious chance to regain their lead with nine minutes remaining. A counter attack saw Fraser find Goodall who in turn played in substitute Scott Adams, but his low strike lacked enough power to trouble Munro.
The match went to penalties, with Goodall thwarted by Munro in Buckie’s first spot-kick.
County converted all their penalties, meaning there was no way back for the Jags when Callachan found the net with their fifth effort.
BUCKIE THISTLE (4-5-1) – Demus 7; Munro 7 (Wood 68), Fyffe 7, Murray 7, Ramsay 6 (McLauchlan 68); MacAskill 7, Fraser 7, Pugh 7, Goodall 8, Barry 8; Urquhart 7 (Adams 79). Subs not used – Herbert, MacKinnon, McCabe, Milne.
ROSS COUNTY (4-2-3-1) – Munro 6; Randall 6, Watson 6, Iacovitti 6, Purrington 5 (Cancola 83); Callachan 6, Paton 7; Edwards 7 (Olaigbe 65), Dhanda 5 (Sims 46), Hiwula 5; White 6 (D Samuel 46) Subs not used – Eastwood, Loturi, MacKinnon, Wright, Smith.
Referee – Chris Graham 6
Man of the match: Max Barry