Bolton
| Round 2 |
Bolton Wanderers |
3–1 |
Walsall |
| Round 3 |
Bolton Wanderers |
2–0 |
Gillingham |
| Round 4 |
Liverpool |
2–3 |
Bolton Wanderers |
| Quarter-final |
Bolton Wanderers |
1–0 |
Southampton |
| Semi-final (1st leg) |
Bolton Wanderers |
5–2 |
Aston Villa |
| Semi-final (2nd leg) |
Aston Villa |
2–0 |
Bolton Wanderers |
| (Bolton Wanderers won 5–4 on aggregate) |
|
Middlesbrough
| Round 2 |
Middlesbrough |
1–0 |
Brighton & Hove Albion |
| Round 3 |
Wigan Athletic |
1–2 |
Middlesbrough |
| Round 4 |
Middlesbrough |
0–0 |
Everton |
| (Middlesbrough won 5–4 on penalties) |
| Quarter-final |
Tottenham Hotspur |
1–1 |
Middlesbrough |
| (Middlesbrough won 5–4 on penalties) |
| Semi-final (1st leg) |
Arsenal |
0–1 |
Middlesbrough |
| Semi-final (2nd leg) |
Middlesbrough |
2–1 |
Arsenal |
| (Middlesbrough won 3–1 on aggregate) |
|
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