Cork City began their second season in the League of Ireland as members of the newly inaugurated Premier Division, but it would prove to be a trying time as, instead of building on the creditable ninth-placed finish of the previous season, they struggled to consolidate their position in the top flight.

The club began the season in the same short-sleeved adidas shirts in which they had finished the previous campaign, though this time with green shorts and socks attached (left, click for larger images). Every so often, however, one of the crest-less shirts from 84-85 would find its way into the kitbag (far left).  In about November or so, the white shorts from the first season returned (below left), the socks following not long after that (below right), but only for a brief period.
Having signed former England international Terry McDermott in the debut season, City repeated the trick the following year as Trevor Brooking made the trip to Cork, albeit for only two games. His arrival coincided with the advent of new long-sleeved shirts, however (right). While the hoops on the main body were the same as on the short-sleeved versions, the neck was plain white, absent of the green trim, with the hoops travelling the length of the sleeves. Another key difference was that crest introduced in 84-85 was now within a circular shield (below left).
Overall, things did not go well for City in the league, with a very poor record at Flower Lodge, and the club were incredibly lucky not to drop down to Division One, surviving on goal difference, with Shelbourne being relegated instead. Things went far better in the FAI Cup, however, as Bray Wanderers and Limerick City were defeated to set up a quarter-final clash against Derry City, who were in their first season in the league. Everywhere they went, the Candystripes brought a massive crowd with them and it was no different for the last-eight tie at the Lodge, the visitors making up about half of the 12,000 attendance. It would be the home supporters who would go home the happier, though, as despite not enjoying home comforts in the league, City took the victory on a 1-0 scoreline courtesy of a goal from sub Ian Hennessy.
Into the semi-finals for the first time, City were presented with a tough task as they were drawn against Shamrock Rovers, who  were seeking a fourth league-and-cup double, and a second in a row. The outcome of the two-legged tie was more or less decided following the first game at Glenmalure Park as Rovers triumphed 4-1, City wearing the same red and white change strip as they had used in 84-85 (right), an outfit which had also been seen away to Bray. While City gave a better account of themselves in the second leg, they were still beaten 4-2, with Rovers claiming an 8-3 aggregate victory, going on to beat Waterford United in the final. Sadly, the semi-final second leg was the last-ever football (association football, anyway) match played at Flower Lodge, with the Ancient Order of Hibernians selling the ground to the Cork County Gaelic Athletic Association Board.