Winton had a good squad in 1999.

Winton Rovers won 4-2 on penalties.
Ardrossan go through to third round of Irvine Times Cup on penalties
Kello kicked off this second round tie (on 25 September 1999) and went straight on the attack keeping Winton pegged back in their own half.  The home side dominated the first half hour but somehow found themselves one behind after a calamity of errors.  A rare flurry up the park by Winton saw Adam Cosgrove cross from the right, but what should have been an easy clearance by Brian Boyd, saw the defender slip on the greasy surface.  The ball ran through to James Hyslop who shot into Andy Black’s left-hand corner and put Ardrossan ahead totally against the run of play.  The Kello players must have been wondering how they went in at half-time losing after complete domination.

Eight minutes into the second half an off-the-ball incident involving Ronnie Caldwell of Kello and Campbell of Winton resulted in Caldwell being shown the yellow card and Ardrossan being reduced to ten men.
  Campbell was shown the red card for his second bookable offence.  In the seventieth minute, Kello got the equaliser their outfield play deserved.  Good close control by Colin Jardine, despite being fouled, was allowed to go on and he played the ball inside to Sam Kerr whose shot from twenty yards seemed to hit a divot and bounced over keeper Watson and into the net.  With two minutes remaining, Dougie Brown should have put the tie out of Kello’s reach. when through on goal but he fired wide to put the game into penalties.  Ardrossan’s five marksman Hyslop, Cosgrove. McCallum, Niven and Brown all scored as did Kello’s McKenzie, Flannagan, Jackson, Kerr and McCreadie.  In sudden death, Ryland scored for Winton but Boyd hit the bar to send the Ardrossan side through.

The teams were:

Kello Rovers - Black, Jackson, McKenzie, Boyd, Flannagan, Caldwell, McCreadie, Brown, Kerr and Jardine with substitutes Nohar, McGhee and Stephen.
Winton Rovers - Watson, Love, Ryland, Gilmour, McCallum, Niven, Cosgrove, Campbell, Hyslop, Latta and Brown with substitutes McNairney, Malcolmson and Donnelly.
Cumnock Chronicle, 1 October 1999