Match ends, East Fife 1, Motherwell 3.
Motherwell needed two extra-time strikes to overcome an intrepid and well-organised East Fife side in the Scottish League Cup second round.
Scott McDonald and Lionel Ainsworth delivered the goals that brought the Premiership side relief at New Bayview.
League Two's East Fife took the lead through the impressive Nathan Austin in the second-half, and looked to be heading for a famous result.
Louis Moult grabbed an equaliser to send the tie into extra-time.
Ian Baraclough's side go into Thursday's third-round draw.
The Premiership side arrived at New Bayview as a team short on form and confidence and East Fife took advantage of that mood of anxiety.
The home side were organised and spirited, while in Austin they had a rangy front man who was capable of alarming the Motherwell centre-backs.
The two clubs are separated by two divisions but the game itself was far more evenly contested.
That was, in large part, down to Motherwell's carelessness on the ball. Much of their passing was hurried or misplaced and the two wide players - Lionel Ainsworth and Marvin Johnson - were peripheral.
The Fifers played conservatively but Austin could be unleashed on his own. One mazy run confused Louis Laing, then the cross was sliced over his own crossbar by Motherwell's Kieran Kennedy. Ross Brown, a busy little midfielder, also rifled a 20-yard shot just wide.
Motherwell's attacks were ponderous but they did manage one break with David Clarkson sliding the ball rough for Ainsworth. The winger stabbed the ball past East Fife goalkeeper Ryan Goodfellow but defender Declan O'Kane was on the line to hack clear.
The ineffective Johnson was replaced at half-time by Dom Thomas and the substitute delivered a smart corner kick that Laing stooped to head wide.
Motherwell would have felt encouraged so early in the second half, but they soon fell to the same failings as the opening period, which enabled East Fife to become more adventurous.
They were rewarded when Kyle Wilkie shouldered aside the hesitant Laing near the touchline before skipping the ball upfield to Austin. The striker took a touch infield before curling a shot past Connor Ripley.
Austin had the ball in the net moments later only for an offside flag to disrupt his celebrations.
Motherwell had brought Scott McDonald on by then to try to rescue the cup tie. Yet East Fife almost doubled their advantage again, with Austin volleying over from close range after Kevin Smith swept the ball in from the left.
The visitors could manage endeavour but enterprise seemed beyond them. From a good position inside the box, Moult saw his effort pushed away by Goodfellow.
But the striker atoned moments later, steering a shot past the goalkeeper from just inside the area.
He should have capped a frantic few minutes by putting Motherwell in front, but he headed Ainsworth's cross just wide.
It said much about the nature of the game that when Austin was substituted late on, he received a standing ovation from the Motherwell fans. East Fife certainly remained full of belief and Wikie's shot had to be tipped over by Ripley.
Motherwell also had a moment to regret, though, with McDonald scooping the ball over from inside the area with only Goodfellow to beat.
He was more clinical just before the interval in extra-time, clipping a shot past Goodfellow from 18 yards after his first effort was pushed away by the goalkeeper.
The victory was secured when Motherwell broke upfield on a counter and McDonald pushed the ball into the path of Ainsworth, who raced into the area and slipped his effort past Goodfellow.
- 14MacGregorSubstituted forNaysmithat 82'minutesBooked at 119mins
- 8BrownSubstituted forMurrayat 94'minutes
- 9AustinSubstituted forSutherlandat 89'minutes
- 18LawSubstituted forWattat 105'minutes
- 14LasleyBooked at 51mins
- 11JohnsonSubstituted forThomasat 45'minutes
- 19ClarksonSubstituted forMcDonaldat 62'minutes
- 20MoultBooked at 110mins
- Barry Cook
- Shots on Target
Second Half Extra Time ends, East Fife 1, Motherwell 3.
Scott McDonald (Motherwell) hits the right post with a right footed shot from outside the box from a direct free kick.
Gary Naysmith (East Fife) is shown the yellow card for a bad foul.
Foul by Gary Naysmith (East Fife).
Scott McDonald (Motherwell) wins a free kick in the attacking half.
Kevin Smith (East Fife) wins a free kick on the left wing.
Foul by Jack Leitch (Motherwell).
Corner, Motherwell. Conceded by Scott Mercer.
Corner, Motherwell. Conceded by Gary Naysmith.
Kevin Smith (East Fife) wins a free kick in the defensive half.
Foul by Joe Chalmers (Motherwell).
Attempt missed. Kevin Smith (East Fife) left footed shot from outside the box is just a bit too high.
Corner, Motherwell. Conceded by Ryan Goodfellow.
Attempt saved. Scott McDonald (Motherwell) right footed shot from outside the box is saved in the bottom right corner.
Louis Moult (Motherwell) is shown the yellow card for a bad foul.
Scott Mercer (East Fife) wins a free kick in the attacking half.
Foul by Louis Moult (Motherwell).
Goal! East Fife 1, Motherwell 3. Lionel Ainsworth (Motherwell) right footed shot from the centre of the box to the centre of the goal. Assisted by Scott McDonald.
Second Half Extra Time begins East Fife 1, Motherwell 2.