1998–99 Football League Cup

The 1998–99 Football League Cup was the 39th staging of the Football League Cup, a knockout competition for England's top 92 football clubs.
The competition began on 11 August 1998, and ended with the final on 21 March 1999, held at Wembley Stadium.
The tournament was won by Tottenham Hotspur, who beat Leicester City 1–0 in the final, thanks to an Allan Nielsen goal in the last minute of normal time.

First round

The 72 First, [Football League Football League Second Division|Second Division|Second] and Third Division clubs compete from the First Round. Each section is divided equally into a pot of seeded clubs and a pot of unseeded clubs. Clubs' rankings depend upon their finishing position in the 1997–98 season.
¹ Team at home in the 1st leg is denoted as the home team

Second round

The 36 winners from the First Round joined the 12 Premier League clubs not participating in European competition in Round Two. First leg matches were played on 15 and 16 September, second leg matches were played on 22 and 23 September.

Tie no	Home team¹	Aggregate	Away team
1	Bristol City	1–3	Crewe Alexandra
2	Coventry City	5–0	Southend United
3	Derby County	2–1	Manchester City
4	Leicester City	6–1	Chesterfield
5	Middlesbrough	3–1	Wycombe Wanderers
6	Norwich City	4–2	Wigan Athletic
7	Q.P.R.	0–3	Charlton Athletic
8	Sheffield Wednesday	1–2	Cambridge United
9	Barnsley	4–1	Reading
10	Blackpool	3–4	Tranmere Rovers
11	Bolton Wanderers	6–3	Hull City
12	Bournemouth	3–2	Wolverhampton Wanderers
13	Brentford	4–6	Tottenham Hotspur
14	Bury	4–2	Crystal Palace
15	Fulham	2–1	Southampton
16	Halifax Town	2–5	Bradford City
17	Huddersfield Town	2–3	Everton
18	Ipswich Town	4–5	Luton Town
19	Leyton Orient	1–5	Nottingham Forest
20	Macclesfield Town	0–9	Birmingham City
21	Northampton Town	2–1	West Ham
22	Portsmouth	3–5	Wimbledon
23	Sheffield United	2–3	Grimsby Town
24	Sunderland	4–0	Chester City

¹ Team at home in the 1st leg is denoted as the home team

Third round

The 24 winners from the Second Round joined the 8 Premiership clubs participating in European competition in Round Three. Matches were played on 27 and 28 October.

Fourth round

Matches were played on 10 and 11 November.
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Quarter-finals

The four matches were played on 1, and 2 December.
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Semi-finals

The semi-final draw was made in December 1998 after the conclusion of the quarter finals. Unlike the other rounds, the semi-final ties were played over two legs, with each team playing one leg at home. The first leg matches were played on 26 and 27 January 1999, the second leg matches were played on 16 and 17 February 1999. It was a narrow victory for Tottenham Hotspur and Leicester City at the expense of Wimbledon and Sunderland, respectively, giving Tottenham the first chance of their major trophy–and place in Europe–for eight years, while Leicester had reached their second final in three seasons.

First leg

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Second leg

Tottenham Hotspur win 1-0 on aggregate
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''Leicester City win 3-2 on aggregate''

Final

The 1999 Worthington Cup Final was played on 21 March 1999 and was contested between Tottenham Hotspur and Leicester City at Wembley Stadium. Tottenham won the match 1–0 thanks to a last minute Allan Nielsen header.