The
1999–2000 League Challenge Cup (known as the
First North Western Trains League Cup for sponsorship reasons) was a knockout competition open to all the league's clubs. The all Division One club final, played at
Bury F.C., was won by
Skelmersdale United 6–5 on penalties following a 0–0 draw (after extra time) against
Newcastle Town.
Semi-finals and Final The semi-finals were decided on aggregate score from two legs played Club's division appended to team name: (D1)=Division One sources: • Semi-finals: • Final: ==Second Division Trophy==