City's second consecutive second-placed finish in the 1999-2000 season meant a fourth season in a row competing in Europe, and in the qualifying round for the UEFA Cup they were pitted against Lausanne of Switzerland (or 'Les Bleus et Blancs', as they are called on the Sportsfile website). Manager Dave Barry would not be leading them in this campaign, however, having decided to step down. Initially, his replacement was Colin Murphy but he only lasted one match before leaving, former Everton and Aston Villa Derek Mountfield taking over. He didn't make any immediate big signings, he did include young full-backs Neal Horgan and Damien Delaney against the Swiss side, City losing 1-0 in each of the legs, the latter drawing over 6,000 to Turner's Cross.

For the two matches, City were forced to comply with stricter UEFA rules on playing kit (far left). The Le Coq Sportif logos were absent from the sleeve while Guinness were the only other company allowed to have their logo on the strip. Slightly different shorts, carrying the mandatory
player numbers, were also worn, with the crest smaller than usual and in plain black. These shorts were also worn in the very early league games with the usual shirt (above), which had the eircom League logo on the sleeve, though the Evening Echo did not feature as a sponsor during this season. Upon its launch during the summer, the new away kit was revealed to be a white shirt with black shorts and socks, but the first away game where a change was required was against Bohemians, where the shorts and socks would have clashed, so the home versions were used instead (right), including the more common numberless shorts.

These shorts also returned to the home strip before too long (left), and while City were doing okay in the league under the new manager, they were not setting the world alight either. The first four games resulted in two wins and two draws, but the next three saw two more draws and a defeat as new signings James Mulligan and Steve Gaughan settled in, though the winless run ended at home to UCD at the start of October. Just a week later, however, City received a fine tonking, losing 4-1 to Shamrock Rovers at the Morton Stadium, despite having signed goalkeeper Michael Devine by this stage. The most notable thing about the kit worn for this match was the addition of red shorts (left), while the back featured the words 'Jazz City' above the numbers as part of Guinness publicising the Cork Jazz Festival, held annually on the October Bank Holiday weekend. Another small change was that the eircom League logo was now housed in a square inside the sleeve stripes rather than on them.

This patch style would also be seen on the away kit worn at Shelbourne two weeks later (right), the first time it was seen with its 'proper' shorts and socks. As far as we can ascertain, those patches were only on the 'Jazz City' away shirts, with the other type used for the remainder of the season (below right), beginning with the St Patrick's Athletic match at the start of November, though the home jersey continued to be used with the newer kind (below left), even if the older ones were occasionally mixed in too.

On the pitch, things were not going all that great, though, a loss away to Longford in early December leaving City in the bottom half of the table, five wins, six draws and five defeats from 16 games leaving them in seventh place as the pressure began to mount (no pun intended) on the new manager, with some fans taking to cultural references from popular TV quiz shows. Longford were also City's opponents in the second round of the FAI Cup, and for the first, drawn, game at Strokestown Road, City wore the home shorts and socks with the away shirts, as they had done for the aforementioned league game.

In between the first match and the replay, City won away to Galway, but contrived to lose at home to Longford to exit the FAI Cup, and they followed that with a loss against Shamrock Rovers and a draw with Shelbourne before St Pat's came to Turner's Cross and won 4-0.

That was the final straw and Mountfield was relieved of his duties, to be replaced by former captain Liam Murphy, who had assisted Mountfield and Dave Barry before him. He effected a turnaround as results began to improve, with City back in the top half of the table after John Caulfield's goal gave them a 1-0 win away to Bohemians at the end of February. For that game, change shorts and socks were required again, but this time City opted to use the red shorts with the home socks (right), creating a fairly lopsided look and, in our view, not doing too much to alleviate the clash which existed as Bohs had so much red on their kit anyway.

From there to the end of the season, City were in scintillating form as Murphy - who was assisted by Patsy Freyne - settled into the job, the team winning six and drawing one of their remaining seven league games, Anthony Buckley playing a key role in midfield. That excellent run was good enough for a third-placed finish in the end with 56 points, four behind runners-up Shelbourne, who City beat 1-0 on the final day to give the title to Bohs for the first time since 1978.