25/04 - 20:00
| 1999/03/21 | Leicester City |  | 0-1 |  | Tottenham |
| 1st Leg | 2nd Leg | |||||||
|---|---|---|---|---|---|---|---|---|
 | (0-3) |  | 0-2 | 0-1 | ||||
 | (1-2) |  | 0-1 | 1-1 | ||||
 | (4-1) |  | 3-0 | 1-1 | ||||
 | (3-4) |  | 2-1 | 1-3 | ||||
 | (4-2) |  | 1-0 | 3-2 | ||||
 | (3-1) |  | 2-0 | 1-1 | ||||
 | (1-3) |  | 1-1 | 0-2 | ||||
 | (5-0) |  | 1-0 | 4-0 | ||||
 | (2-1) |  | 1-1 | 1-0 | ||||
| (6-1) |  | 3-0 | 3-1 | ||||
 | (6-3) |  | 3-1 | 3-2 | ||||
 | (3-2) |  | 1-1 | 2-1 | ||||
 | (1-5) |  | 1-5 | 0-0 | ||||
 | (0-9) |  | 0-3 | 0-6 | ||||
 | (3-5) |  | 2-1 | 1-4 a.e.t. | ||||
 | (2-3) |  | 2-1 | 0-2 a.e.t. | ||||
 | (4-5) |  | 2-1 | 2-4 a.e.t. | ||||
 | (2-3) |  | 1-1 | 1-2 | ||||
 | (4-6) | | 2-3 | 2-3 | ||||
 | (4-2) |  | 3-0 | 1-2 | ||||
 | (2-1) |  | 1-1 | 1-0 | ||||
 | (2-5) |  | 1-2 | 1-3 | ||||
 | (4-0) |  | 3-0 | 1-0 | ||||
 | (2-1) |  | 2-0 | 0-1 |
| 1st Leg | 2nd Leg | |||||||
|---|---|---|---|---|---|---|---|---|
| (4-3) |  | 3-2 | 1-1 | ||||
| (0-0) |  | 0-0 | 0-0 (7 pens-6) | ||||
| (4-2) |  | 2-1 | 2-1 | ||||
| (3-2) |  | 1-1 | 2-1 a.e.t. | ||||
| (5-4) |  | 2-3 | 3-1 | ||||
 | (1-9) | | 0-2 | 1-7 | ||||
| (3-2) |  | 2-1 | 1-1 a.e.t. | ||||
| (3-2) |  | 3-1 | 0-1 | ||||
 | (2-6) | | 1-1 | 1-5 | ||||
| (2-1) |  | 1-0 | 1-1 | ||||
| (2-1) |  | 1-0 | 1-1 | ||||
| (3-1) |  | 2-0 | 1-1 | ||||
 | (2-6) | | 2-1 | 0-5 | ||||
| (4-0) |  | 1-0 | 3-0 | ||||
| (2-1) |  | 1-1 | 1-0 | ||||
| (5-2) |  | 1-1 | 4-1 | ||||
| (7-4) |  | 4-0 | 3-4 | ||||
 | (3-4) | | 3-2 | 0-2 | ||||
 | (1-3) | | 1-1 | 0-2 | ||||
 | (1-3) | | 0-0 | 1-3 a.e.t. | ||||
| (4-0) |  | 3-0 | 1-0 | ||||
 | (2-3) | | 1-1 | 1-2 a.e.t. | ||||
 | (2-4) | | 2-1 | 0-3 | ||||
| (2-0) |  | 1-0 | 1-0 | ||||
| (4-3) |  | 2-0 | 2-3 | ||||
 | (2-2) | | 0-2 | 2-0 (2 pens-4) | ||||
 | (2-3) | | 2-1 | 0-2 | ||||
 | (1-2) | | 1-1 | 0-1 a.e.t. | ||||
 | (0-3) | | 0-1 | 0-2 | ||||
 | (3-4) | | 1-2 | 2-2 | ||||
 | (3-6) | | 1-3 | 2-3 | ||||
 | (0-4) | | 0-1 | 0-3 | ||||
| (5-3) |  | 3-1 | 2-2 a.e.t. | ||||
 | (2-2) | | 2-2 | 0-0 | ||||
| (2-0) |  | 1-0 | 1-0 | ||||
 | (1-4) | | 0-2 | 1-2 |
| 2 |
|
Chris Armstrong Tottenham | 5 G |
| 2 |
|
Tony Cottee Leicester City | 5 G |
| 2 |
|
Mark Stein Bournemouth | 5 G |
| 5 |
|
Michael Bridges Sunderland | 4 G |
