This page shows the winners of the cups for the 1999-00 season that are fully featured in the FCHD.
| F.A. Cup | Won by Chelsea |
| F.A. Trophy | Won by Kingstonian |
| F.A. Vase | Won by Deal Town |
| Football League Cup | Won by Leicester City |
| Football League Trophy | Won by Stoke City |
Other Cup competitions, not fully featured in the FCHD
| F.A. Sunday Cup | Won by Prestige Brighams |
| Capital Counties Feeder Leagues Trophy | Won by Tring Athletic |
| Amateur Football Alliance Senior Cup | Won by U C L Academicals |
| Welsh Cup | Won by Bangor City |
| F.A.W. Premier Cup | Won by Wrexham |
| Scottish Cup | Won by Rangers |
| Scottish League Cup | Won by Celtic |
| Scottish League Challenge Cup | Won by Alloa Athletic |
| Scottish Junior Cup | Won by Whitburn |
Please credit the F.C.H.D. when using this information elsewhere