The Lilywhites first met the former Football League Club, Glossop North End on October 3rd, 1998. Originally founded in 1886 as Glossop North End, the Derbyshire side had been members of the Football League from 1898 until 1915 as Glossop F.C. but by the time they played the Lilywhites in 1998 were in the North West Counties League Division One. They had reverted to their original name, Glossop North End, in 1992.
3.10.1998 Cambridge City 1 - 1 Glossop North End 2nd Qualifying Round Cambridge City team: Paul Barber, Marvin Harriott, Jason Carter, Steve Holden, Jamie Saddington, Steve Greaves, Terry Robbins, Ian Brown, Andy Kiwomya, Adie Cambridge and Neil Cogger. Subs used by the Lilywhites were Mark Adams for Greaves and Phil Starbuck for Kiwomya. Kiwomya scored the Lilywhites goal.
6.10.1998 Glossop North End 1 - 1 Cambridge City 2nd Qualifying Round Replay Cambridge City team: Barber, Harriott, Richard Chattoe, Holden, Saddington, Mark Reeder, Robbins, Brown, Starbrook, Cambridge and Cogger. Subs used were Michael Egan for Saddington and Lee Owen for Robbins. Phil Starbrook was making his full debut in a match that the Lilywhites were to lose 5-4 on penalty despite playing most of the game in their opponents half. Despite being one up at half-time, thanks to a goal by Starbroook in the 23rd minute, the Lilywhites could not increase their lead. Then against the run of play, Glossop equalised from their own chance of the game. This took the match into extra time and that was the score it remained. So then it was down to penalties. With these locked at 4 all, after Starbrook, Cambridge, Brown and Owen had scored for the Lilywhites, Chattoe missed his and with Glossop scoring their fifth, the Lilywhites F.A. Cup run was over again for another season.
Programme produced by Glossop at short notice for the replay