Tayport were left bitterly disappointed last Saturday when they lost out to Forfar West End on the Canniepairt and exited the Consolation Cup at the group stage.
The home team had the better of the first half and they put themselves on course for the quarter-finals.
Jamie Mackie set up Josh Chalmers to net, but the midfielder was offside.
On 26 minutes Tayport took a deserved lead.
Player-coach Willie Campbell charged down a clearance in midfield and the ball found its way through to Robertson who skipped past defender George and was taken down.
Robertson himself struck the penalty kick high into the net.
Jack Shaw had to save a free kick from West End, while, at the end of the half, Daryl McKenzie got in a header from a corner which smacked against the inside of the post.
Two minutes into the second half, the visitors pulled level.
A free kick was lofted into the home box and the ball fell Gary Robertson and he fired in the equaliser.
Minutes later, a quick break upfield caught Tayport out.
They failed to clear their lines and visiting Montgomery was sharpest and he swept the ball past Shaw and Forfar were now in the driving seat.
Luke O’Brien tried his luck from distance for ‘Port, but West End remained dangerous and Cameron McMahon soon grabbed their third goal.
Needing a win to progress, Stevie Kay’s men were now up against it, but they did fashion some openings.
An Inglis shot beat the ‘keeper, but Cruickshanks cleared off line and, on 83 minutes, Struan Christie slipped the ball through to Lewis Payne and he too was thwarted.
With five minutes to go Jamie Mackie was felled inside the box, giving Tayport their second penalty of the match.
This time, Dayle Robertson saw his kick saved and that summed up Tayport’s day.
Tayport: Shaw, Rollo (Christie), Sturrock, O’ Brien, Suttie (Liversedge), Campbell (Payne), Gill, Inglis, Robertson, Mackie, Chalmers.