Boro 0 - 1 Rainworth MW
The game was a scrappy one from start to finish, and the deciding goal came deep into the second half of extra time.
The first half saw the visitors on top. A powerful header bounced off the bar onto the line after 26 minutes, with many of the Rainworth players and supporters suspecting that it was over the line.
Just six minutes later, Barry Alberry smashed a free kick from the left of the area onto Glenn Powley's left hand post.
Just before the half time break, Craig Wilson sprinted through the Boro defence and found himself one on one with Powley, but somehow scooped his shot left of the goal resulting in a goal kick for Scarborough.
Boro's first real chance of the game came after 59 minutes, with Craig Evans firing a shot in from 25 yards, which rifled agonisingly wide as Mark Hales in the Rainworth goal was desperately scrambling across his line.
Five minutes later, Mark Shaw should have put Rainworth ahead. A ball from the right into the Boro penalty area was picked up by Shaw, who from six yards out pulled the ball wide of Powley's goal when it looked easier to score.
The save of the game came after 64 minutes, where a long range shot was heading into the bottom left hand corner of Powley's goal, but he somehow managed to dive across and clear it for a Rainworth corner.
As time wore on, it seemed obvious to the 401 supporters in attendance that the game was heading for extra time, and possibly penalties.
After six tense injury time minutes, the referee blew up and signalled that there was to be an extra thirty minutes of play.
The first chance of the second half fell, as they seemed to all evening, to Rainworth. Substitute Steve Shannon somehow pulled his shot wide from 3 yards out - surely the best chance of the evening.
Just a moment later, it was Liam Widdowson who blasted a 25 yard shot in, but again it bounced tantalisingly wide of the left hand post.
As half time in extra time approached, Boro had perhaps their best chance of the evening. Matty Kennett was left unmarked from a corner on the edge of the box. He fired a shot low at goal, but Mark Hales pulled off a fantastic save. This was to be Boro's last good chance of the evening.
A key incident in the match came after 104 minutes, where Powley came charging out of his box to intercept Steve Shannon who was through on goal. As he attempted to clear, and get his entire body behind it, he handballed it to safety. Everyone in the ground was suspecting a straight red card, but a yellow was produced, much to the disgruntlement of the travelling players and fans.
Just one minute later, an uncannily identical situation. This time, Powley came out and missed the ball, but Shannon scooped it well wide of goal after he managed to lob the keeper.
The second half of extra time yielded the only goal of the game. On 109 minutes, a cross in from the left found Rainworth's midfielder Richard Smith, who blasted it low into the centre of the goal. Powley got down to it, and indeed got a hand to it, but couldn't stop it sneaking in at the far post. Rainworth had the lead with just ten minutes left, and their players were ecstatic, wheeling away and circling half the pitch in celebration.
Two minutes later, and perhaps another potential sending off. Simon Poxon of Rainworth scythed down Craig Smethurst, and understandably, the Boro man said something in return. Poxon then proceeded to push Smethurst in the chest on several occasions, right in front of the referee. Remarkably, both players got away with a strong telling off from the man in black.
This was to be the last action of an entertaining, but ultimately disappointing game for Scarborough, as they bowed out of the Wilkinson Sword at the first time of asking.
One of the downsides of the evenings game was seeing Joe Lightowler limping off after 79 minutes. He was seen on crutches after the match, so hopefully he won't be out for too long.
A few changed were made to the side, which may reflect on how the management view Saturday's home league fixture with Barton Town Old Boys with more importance.
Scarborough Athletic: Glenn Powley, Jon Ellwood, Craig Evans (Lee Cappleman 110), Ryan Davies (C), Matty Kennett, Scott Phillips, Mark Griffin, Liam Widdowson, Joe Lightowler (Alex Reveley 79), Craig Hogg, Martyn Ferrey (Craig Smethurst 50)
Rainworth MW: Mark Hales, Glenn Nattriss, Adam Fletcher, Lee Wilkinson (C), Simon Poxon, Matt Draper, Richard Smith, Barry Alberry, Robbie Clarke (Adam Lilley 5 (Steve Shannon 45)), Craig Wilson, Mark Shaw.
Sub not used: Malcom Brown
Scarborough Athletic: Powley, Ellwood, Davies, Kennett, Phillips
Rainworth MW: Smith, Lilley, Shannon
Rainworth MW: Richard Smith 109'
Match report thanks to Matt Lawson - SAFC PA and webmaster of sea-siders.co.uk