Raith Rovers made Ross County manager Derek Adams pay for making sweeping changes by dumping the top-flight newcomers out of the League Cup.
Greig Spence opened the scoring for the First Division side from close range after 25 minutes.
Allan Walker set-pieces either side of the break led to headed goals from Brian Graham and Douglas Hill.
Graham fired his second of the night and ninth of the season after 63 minutes before Russell Duncan's reply.
Had it not been for former Celtic and Hibernian goalkeeper Mark Brown, making his debut after signing a short-term contract, it could have been a more heavy defeat for the Dingwall outfit.
Brown was one of nine changes made by Adams following Saturday's win over Dundee as he makes survival in the Scottish Premier League his priority this season.
Summer signings Jonathan Bateson, Mihael Kovacevic and Gary Glen were handed their debuts, while Paul Lawson, Martin Scott, Sam Morrow, Kurtis Byrne and Duncan came back into the side.
Rovers player-manager Grant Murray had made only one change from the team that drew 0-0 with Livingston, with Spence replacing midfielder Grant Anderson and the former Celtic striker had already threatened with an overhead kick before breaking the deadlock.
Graham slipped the ball through to Walker, who in turn teed it up for Spence for the easiest of tasks of guiding the ball into the net.
County had threatened first through a couple of Morrow headers and they responded to the goal with a stinging shot from Byrne that was held by McGurn.
Experienced Rovers defender Laurie Ellis hobbled off to be replaced with Colin Wilson on the half-hour mark, but the visitors were not put off their stride and Pat Clarke flashed a shot narrowly wide of the far post.
From Walker's inswinging corner, Graham sent a bullet header into the net at the near post four minutes before the break.
It got worse for County in the 51st minute when Walker swung over a free-kick from the right and Hill rose above everyone to head powerfully into the net.
With the Dingwall side in disarray, Walker's shot inside the box was blocked and Graham latched on to the loose ball and drilled it into the far corner of the net.
Brown denied Clarke with a fine save before Duncan prodded County's reply over the line after 84 minutes.
Ross County manager Derek Adams : "I made nine changes, but the players who came in didn't perform well enough.
"The players who came in tonight have missed a huge opportunity, they slide further down the pecking order.
"The players who had the jersey last Saturday, have the jersey for this Saturday.
"I gave the players an opportunity, we don't have reserve-team football now and had a squad that was more than capable of playing here tonight."
Raith Rovers player - manager Grant Murray : "We knew when the draw was made it would be a difficult game, but I can't give my players enough credit for the performance they put on tonight.
"We saw they had made changes before the game, but they still had experienced players in their team.
"I thought my players were magnificent. To go that well ahead against an SPL team, it was great for the guys, they truly deserved it.
"We knew they would come out in the second half and have a go and if they had scored then it might have been a different game."
- 25 Brown
- 02 Bateson
- 03 Fitzpatrick Booked
- 05 Boyd
- 22 Kovacevic
- 08 Lawson
- 14 Scott
- 18 Duncan
- 17 Morrow
- 19 Byrne
- 20 Glen
- 01 Fraser
- 04 Munro
- 23 Macphee
- 12 Quinn
- 24 Ross
- 01 McGurn
- 02 Thomson
- 03 Malowne
- 04 Ellis (Wilson - 30' )
- 05 Hill
- 06 Anderson
- 07 Spence (Anderson - 78' )
- 08 Walker
- 11 Hamill (Callachan - 83' )
- 09 Graham
- 10 Clarke
- 17 Laidlaw
- 15 Murray
- 16 Wilson
- 12 Anderson
- 14 Callachan
Live Text Commentary
Full Time The referee ends the match.90:00 +0:50
Paul Lawson decides to take a short corner.87:05
Russell Duncan challenges Pat Clarke unfairly and gives away a free kick. Direct free kick taken by Allan Walker.86:17
Free kick awarded for a foul by Pat Clarke on Martin Scott. Free kick taken by Mark Brown.85:29
Unfair challenge on Edward Malowne by Martin Scott results in a free kick. Free kick taken by Edward Malowne.84:43
Martin Scott challenges Stuart Anderson unfairly and gives away a free kick. Free kick taken by Stuart Anderson.83:27
Martin Scott provided the assist for the goal.83:27 Goal scored
Goal! - Russell Duncan - Ross Co 1 - 4 Raith Russell Duncan finds the back of the net with a goal from inside the six-yard box to the bottom left corner of the goal. Ross County 1-4 Raith.83:07
Free kick awarded for an unfair challenge on Scott Boyd by Brian Graham. Direct free kick taken by Mark Brown.82:39 Substitution
Substitution Ross Callachan replaces Joe Hamill.82:07
Gary Glen produces a left-footed shot from just outside the box that misses to the right of the net.80:36
Free kick taken by David McGurn.80:36 Booking
Booking Marc Fitzpatrick is cautioned by the ref for unsporting behaviour.80:20
Foul by Marc Fitzpatrick on Grant Anderson, free kick awarded.77:45 Substitution
Substitution Greig Spence goes off and Grant Anderson comes on.77:45
Free kick awarded for an unfair challenge on Paul Lawson by Allan Walker. Direct free kick taken by Mark Brown.77:15
Foul by Paul Lawson on Allan Walker, free kick awarded. David McGurn restarts play with the free kick.76:39
Free kick awarded for a foul by Pat Clarke on Jonathan Bateson. Mark Brown restarts play with the free kick.75:06
Mihael Kovacevic challenges Brian Graham unfairly and gives away a free kick. Edward Malowne takes the free kick.73:05
Paul Lawson gives away a free kick for an unfair challenge on Greig Spence. Allan Walker produces a strike on goal direct from the free kick, save by Mark Brown.
Mihael Kovacevic takes a shot.71:57
Inswinging corner taken right-footed by Paul Lawson from the right by-line, Brian Graham manages to make a clearance.71:30
Douglas Hill challenges Gary Glen unfairly and gives away a free kick. Free kick taken by Paul Lawson.70:35
Pat Clarke takes a shot. Save made by Mark Brown.67:38
Brian Graham gives away a free kick for an unfair challenge on Mihael Kovacevic. Free kick taken by Mihael Kovacevic.65:25
Pat Clarke takes a shot. Save made by Mark Brown.62:36
Assist on the goal came from Allan Walker.62:36 Goal scored
Goal! - Brian Graham - Ross Co 0 - 4 Raith Brian Graham fires in a goal from inside the penalty box to the bottom left corner of the goal. Ross County 0-4 Raith.62:01
Unfair challenge on Brian Graham by Mihael Kovacevic results in a free kick. Direct free kick taken by Edward Malowne.61:09
Outswinging corner taken from the right by-line by Paul Lawson, Allan Walker manages to make a clearance.60:07
Corner from the left by-line taken by Allan Walker, Martin Scott manages to make a clearance.59:29
Outswinging corner taken left-footed by Joe Hamill, clearance made by Russell Duncan.58:13
Paul Lawson challenges Pat Clarke unfairly and gives away a free kick. Pat Clarke fires a strike on goal direct from the free kick, save by Mark Brown.57:05
Edward Malowne takes a shot. Save by Mark Brown.55:39
Pat Clarke takes a shot. Save by David McGurn.53:54
Jonathan Bateson gives away a free kick for an unfair challenge on Pat Clarke. Direct free kick taken by Joe Hamill.50:58
Allan Walker provided the assist for the goal.50:58 Goal scored
Goal! - Douglas Hill - Ross Co 0 - 3 Raith Douglas Hill grabs a headed goal from inside the six-yard box. Ross County 0-3 Raith.50:03
Gary Glen challenges Pat Clarke unfairly and gives away a free kick. The free kick is delivered right-footed by Allan Walker from right wing,48:23
Outswinging corner taken right-footed by Paul Lawson from the right by-line.47:47
Gary Glen takes a shot. Save by David McGurn.47:00
Brian Graham gives away a free kick for an unfair challenge on Scott Boyd. Direct free kick taken by Mark Brown.46:14
Allan Walker takes a shot. Save made by Mark Brown.45:13
Pat Clarke produces a right-footed shot from just outside the box that misses to the right of the net.45:01
The referee starts the second half.45:00 +0:12 Half time
Half Time The ref blows to signal half-time.41:43
Kurtis Byrne takes a shot. David McGurn makes a save.40:13
Assist by Allan Walker.40:13 Goal scored
Goal! - Brian Graham - Ross Co 0 - 2 Raith Brian Graham finds the net with a headed goal from inside the six-yard box. Ross County 0-2 Raith.39:14
Corner taken right-footed by Allan Walker,37:42
Corner taken right-footed by Allan Walker from the left by-line to the near post, clearance made by Martin Scott.35:46
Pat Clarke has an effort at goal from outside the box which goes wide right of the target.35:11
Corner taken by Allan Walker from the left by-line, Sam Morrow manages to make a clearance.33:25
Foul by Colin Wilson on Russell Duncan, free kick awarded. Shot comes in from Paul Lawson from the free kick.31:09
Free kick awarded for a foul by Mihael Kovacevic on Pat Clarke. Allan Walker takes the free kick.30:47
Kurtis Byrne has an effort at goal from outside the penalty box which goes wide right of the target.30:04
Allan Walker challenges Kurtis Byrne unfairly and gives away a free kick. Marc Fitzpatrick takes the direct free kick.29:25 Substitution
Substitution Colin Wilson is brought on as a substitute for Laurence Ellis.26:17
Outswinging corner taken by Paul Lawson from the right by-line, clearance by Jason Thomson.24:51
The assist for the goal came from Joe Hamill.24:51 Goal scored
Goal! - Greig Spence - Ross Co 0 - 1 Raith Greig Spence scores a goal from close in low into the middle of the goal. Ross County 0-1 Raith.19:03
Effort on goal by Kurtis Byrne from outside the box goes harmlessly over the bar.18:36
The assistant referee flags for offside against Pat Clarke. Free kick taken by Mark Brown.14:54
Brian Graham produces a right-footed shot from just outside the box that goes wide right of the goal.14:16
Effort from inside the six-yard box by Greig Spence goes wide right of the target.12:02
Free kick awarded for an unfair challenge on Scott Boyd by Brian Graham. Mark Brown restarts play with the free kick.11:40
Sam Morrow takes a shot. Save by David McGurn.10:03
Martin Scott gives away a free kick for an unfair challenge on Pat Clarke. Free kick taken by Edward Malowne.8:44
Foul by Russell Duncan on Joe Hamill, free kick awarded. Free kick taken by Allan Walker.7:52
Martin Scott gives away a free kick for an unfair challenge on Pat Clarke. Edward Malowne takes the direct free kick.6:45
Header from deep inside the penalty area by Sam Morrow goes harmlessly over the crossbar.2:02
Joe Hamill fouled by Martin Scott, the ref awards a free kick. Joe Hamill restarts play with the free kick.0:40
Pat Clarke is adjudged to have handled the ball. Free kick taken by Jonathan Bateson.0:00
The referee starts the match.
Live data and text provided by our data suppliers