Inside normal time, the Bonny Blues took the lead when record-breaking scorer Martyn Coleman, who broke Steven Rigg’s record for most goals by a Penrith player in a season, added goal number 46 to his extraordinary tally for the campaign.
But Workington Reds brought on their three substitutes during the second half with one of those, Scott Allison, levelling the scores and forcing extra-time.
And Symington found the bottom corner to ensure Reds retained the trophy.
Penrith were straight on the front foot at the start of the match, with top scorer Coleman winning a corner inside a matter of seconds.
There was then a delay of around three minutes with Matty Moynan going down, although he was fit enough to come back on after an entertaining opening few minutes.
But, despite the early action, neither side were able to create any real opportunities of note in an even start to the game.
This was until the 20th minute when hitman Coleman broke down the right, hurdled a challenge and cut the ball back to right-back Ric Faustino, who fired over from inside the penalty box.
Six minutes later an effort from Workington Reds’ Robbie Hebson, who also played for Jim Nichols’ Penrith this term, was dragged narrowly wide of Penrith keeper Jonny Jamieson’s left-hand post.
Coleman was certainly proving to be the biggest threat for the Workington defence to deal with after a season in which he broke the club’s goal-scoring record. He was looking to end the campaign in style by adding to his incredible 45 goals so far this term, before the final.
Penrith thought they had taken the lead on the half hour mark when Reds keeper Tom Fowler spilled Coleman’s original effort, with Kevin Connelly slotting in the loose ball. But the goal was ruled out for offside.
Nathan Waterston did well to find space just outside the box on Carlisle United’s Brunton Park pitch with 36 minutes on the clock. His effort, though, was well off target.
Jamieson was then called into his first real action of note as he plucked a cross out of the sky, despite the close attention he was receiving from Hebson at the back post.
The Bonny Blues broke the deadlock shortly before half-time in the final when ex-Workington Reds man Coleman won a free-kick and then took it himself. His set-piece took a slight deflection off the wall but found its way into Fowler’s net.
Reds joint bosses Dave Hewson and Lee Andrews opted to make changes at half-time, with former Carlisle United man Symington and Jake Simpson on in place of Calum Henderson and Hebson.
But it was Nichols’ men who had the first chance four minutes after the restart. Connelly floated in a cross for Andy Murray-Jones who had found space in Reds’ box, although he missed the ball completely.
Workington opted to use their final throw of the dice on the hour mark, with Scott Allison replacing Waterston.
On 65 minutes, Reds substitute Allison bent a strike wide of Jamieson’s left-hand post, with Sam Joel lurking but unable to connect with the ball as he tried to reach it at the back post.
By and large, the Bonny Blues looked comfortable holding on to their advantage after taking the lead.
But Workington Reds drew level on 78 minutes when Allison managed to flick a cross from fellow substitute Symington past Penrith keeper Jamieson.
Penrith had a big chance to retake the lead when Coleman turned past the Reds defence nine minutes from time. He unselfishly looked for Read but his attempted cross, which had taken goalkeeper Fowler out the game, was cut out and the danger was cleared.
Five minutes later, Coleman drilled a ball across goal which looked like it had left Connelly with an open net, only for Simpson to put him under enough pressure at the back post. At the other end, Reds replied with an opportunity of their own with both teams looking for a crucial late breakthrough.
Though, given the fact both teams needed penalties to progress from their respective semi-finals against Carlisle City and Pirelli, it is perhaps little surprise that this wasn’t decided inside 90 minutes.
Reds had the better chances in the first period of extra-time, although the game remained level as the 105 minutes of football started to take its toll on both sets of players.
Penrith felt they had a case for a penalty on the 111th minute after a handball, however instead, a foul was given the other way after the overhead kick.
Seconds later, at the other end, Joel blasted over the top with a glorious opportunity for Reds.
The match looked set for penalties before Symington, who had scored in Workington’s play-off semi-final, slotted into Jamieson’s bottom corner with just two minutes to play to ensure it was skipper Kyle May lifting the Cumberland Cup.
Penrith keeper Jamieson got his head to a corner in the dying seconds, although his effort went over the bar and Cumberland Cup holders Workington Reds retained their trophy.
Both sides were without experienced men as Penrith’s long-serving defender Will Paul and Workington Reds captain Gari Rowntree missed out through respective injuries.
Reds opted to go with some of the squad players that had helped them reach the final, with some of their regular first-team players, such as Simpson, Josh Calvert and Symington, named on the substitute’s bench. Dan Wordsworth was also not in the Workington squad, with May captaining the team on the night.
Comments: Our rules
We want our comments to be a lively and valuable part of our community - a place where readers can debate and engage with the most important local issues. The ability to comment on our stories is a privilege, not a right, however, and that privilege may be withdrawn if it is abused or misused.
Please report any comments that break our rules.
Read the rules here