Another season, another change of manager, another almost-unnoticeable tweak to the design of the home kit. Despite manager Eamonn O'Keefe's hopes that City could push on from the wins in the previous season's Opel League Cup and Munster Senior Cup wins, early-season league form was not an improvement on what had gone before. That, combined with the average attendance figure remaining low, meant that O'Keefe was relieved of his managerial duties, with his predecessor Noel O'Mahony returning for a second spell in charge.

The kit was a hybrid of the previous two seasons (top left), with the 1986-87 v-neck returning while the 87-88 white sleeves remained (though the adidas logos were now black rather than red). In addition, the adidas logo and City crest returned to the hoop immediately above the Guinness wordmark. The club began the season in green shorts and socks, but midway through the campaign the white versions returned (middle left). When a change was required, the red and white kit from the previous season was retained, but his time was paired with red shorts (top right).

The fairly average league performances continued, with City dropping a spot to eighth, garnering 26 points from 33 games played. Over the course of the season, two clothing anomalies arose, with the upshot that some games saw three different jersey variations used. At some stage, the number 11 shirt went missing, meaning that John Caulfield was required to don the 87-88 version (right), while a rogue number 4 jersey, with all of the frontal markings higher than on the rest, also crept into the kit bag (bottom right).

Despite these inconsistencies, the club somehow managed to piece together a good run of form in the FAI Harp Lager Cup, defeating Sligo Rovers, Cobh Wanderers and Dundalk (after a replay) to reach the two-legged semi-final, where they face Bray Wanderers. In the first game at Turner's Cross, Bray came away with a 1-0 win thanks to Eugene "Pooch" Davis's goal, but a week later at the Carlisle Grounds City avenged that defeat as Philip Long scored the only goal from a penalty. Dave Barry nearly put City through but hit the crossbar in the last minute, meaning a replay, scheduled for Turner's Cross the next Wednesday.

For the first leg, Bray, who wore green and white stripes that season, wore their white away with green shorts against City's hoops, but for the replay it was decided that both teams should change. City, in their red and white, triumphed on a 4-0 scoreline (Barry with two, John Caulfield getting one while there was also an own goal) to progress to the final against Derry City, who would be going for a domestic treble. To mark the occasion of reaching the final of the blue-riband competition for the first time, adidas produced a brand-new strip for City, the first time that the home kit would not be hooped (left).

With predominantly white shirts, the main design feature was a green and red zig-zag based on the West Germany shirts at the previous year's European Championship, with green shorts and socks once again returning. In addition, there was an inscription above the crest (bottom left). The new kit almost proved to be a lucky charm but once again Barry was denied by the woodwork, this time hitting the post in the scoreless game at Dalymount Park on May 1. As with the quarter-final and semi-final, City would have to compete in a replay, but a week later their luck ran out as Felix Healy's goal gave Derry a 1-0 win.