Ipswich Town historical cup results 1999/2000
Full listing of knockout competition results during the season
| F.A. Cup sponsored by AXA | ||||||
|---|---|---|---|---|---|---|
| 3rd Round | Mon 13 Dec | Ipswich Town (LD1) | 0 - 1 | Southampton (PREM) | ||
| Worthington League Cup | ||||||
|---|---|---|---|---|---|---|
| 1st Round 1st Leg | Wed 11 Aug | Brentford (LD2) | 0 - 2 | Ipswich Town (LD1) | ||
| 1st Round 2nd Leg | Tue 24 Aug | Ipswich Town (LD1) | 2 - 0 | Brentford (LD2) | ||
| Ipswich Town won 4-0 on aggregate | ||||||
| 2nd Round 1st Leg | Tue 14 Sep | Crewe Alex. (LD1) | 2 - 1 | Ipswich Town (LD1) | ||
| 2nd Round 2nd Leg | Tue 21 Sep | Ipswich Town (LD1) | 1 - 1 | Crewe Alex. (LD1) | ||
| Crewe Alexandra won 3-2 on aggregate | ||||||
| Football League Play-Offs (Lvl 2) | ||||||
|---|---|---|---|---|---|---|
| Semi Final 1st Leg | Sun 14 May | Bolton Wdrs. (LD1) | 2 - 2 | Ipswich Town (LD1) | ||
| Semi Final 2nd Leg | Wed 17 May | Ipswich Town (LD1) | 5 - 3 | Bolton Wdrs. (LD1) | ||
| after extra time, 90 minutes 3-3, Ipswich Town won 7-5 on aggregate | ||||||
| Final | Mon 29 May | Ipswich Town (LD1) | 4 - 2 | Barnsley (LD1) | ||
| played at Wembley | ||||||
