The summer of 1999 brought a big change for Cork City as, for the first time, the kits would be manufactured by a company other than adidas, as the club signed a deal with Le Coq Sportif. The French company's first offering would not turn out to be hugely different from the kit it replaced, with the white horizontal band remaining, though white side panels were added and the collar was now red.

The new strip was first worn competitively in the UEFA Cup against IFK Gothenburg in August, City losing 3-0 away before Pat Morley's goal gave them a 1-0 win in the second leg. For these games, and the early league matches, Guinness was the only sponsor - in a new wordmark and featuring the famous harp for the first time - and numbers appeared on the shorts (far left). Before long, however, the Evening Echo patches were added to the sleeves, along with logo of the league's new sponsors eircom, while Top Car's logo was back on the shorts, the numbers curiously being jettisoned (left). The crest also received a facelift (below left).
Former Manchester United, Newcastle United and Republic of Ireland midfielder Liam O'Brien had been signed on a free transfer from Tranmere Rovers and he added creativity - if not workrate - to the midfield and a positive start included a 1-0 win over champions St Patrick's Athletic, though there was also a sloppy home reverse to Sligo Rovers. The third league game of the season saw City away to Galway United, which was a first outing for the new away kit, which was a real departure. While the general design followed that of the home, without the band and with a button-up collar, it was the colour which was unusual, cream with black trim (top right). If one were cynical, one might out that those are also the colours of Guinness, though if it were the case that it was promotional tie-in, a trick was missed with the socks, which would have been better has they had solid cream turnovers to resemble a pint. Top Car had been added to the away shorts for the return fixture with St Pat's in November.
While that game in Richmond Park was lost, overall results remained good and City had reached the top of the table, a highlight being the 5-0 away win against Sligo in mid-November. Unsurprisingly, John Caulfield and Pat Morley were on target in that game, but a hat-trick for Colin O'Brien could scarcely have been expected. For kit aficionados/nerds, however, that game provided a source of anticipation as Sligo's home kit this season was white with a red hoop and it might have been expected that a third kit would be called into action. While Le Coq had produced a green shirt in the same design as the home, this was never worn by the first team and the cream away provided enough differentiation.

Instead, the next kit 'change' came at home in a top-of-the-table clash with Shelbourne at the start of December, with long-sleeved home shirts worn, with the Le Coq small sleeve logos noticeably lower than on the short-sleeved versions. Disappointingly, for St Pat's in 1998-
99 read Shels in 99-00 as the Dublin side won 2-1 at Turner's Cross to move three points clear at the top and they would remain at the summit for the rest of the season. Disappointing draws away to UCD and at home to Waterford United immediately followed that defeat before another loss, 3-0 away to Bohemians on December 27. This game was noticeable for City wearing the home socks with the away kit (right) due to a clash with Bohs' black, seemingly the only instance of mixing and matching during the season.

Even at that relatively early stage, the league looked done and dusted as Shelbourne were just so much better than everybody else, and though City were the best of the rest, results were far too inconsistent for any hope to be held out that a late charge at the title could yield anything. A five-game run starting in mid-January saw a 0-0 draw away to Drogheda United, another scoreless draw at home to Derry City, 1-1 away to Finn Harps, 0-0 at home to Sligo and 1-1 at home to Pat's. A different result was finally achieved away to Shels but unfortunately it was a 4-0 loss, just to fully extinguish any hopes, with long-sleeved away shirts worn, without the Evening Echo sleeve logos for some reason (right).

As the end of the season loomed, City finally remembered how to win, victories over Bohemians, Shamrock Rovers, Drogheda and Derry enough for a second consecutive second-placed finish, though the 58-point haul was 11 behind the champions Shels. Having intimated after the 98-99 season that he was considering retirement, manager Barry went through with that decision during the close season, meaning more upheaval ahead of the 2000-01 season, though what would follow was notable even by City's standards.