1999 in Estonian football
Meistriliiga champions
FC Levadia Tallinn
Esiliiga champions
FC Kuressaare
Estonian Cup winners
FC Levadia Tallinn
Estonian Super Cup winners
FC Levadia Tallinn
Teams in Europe
FC Flora Tallinn JK Tulevik Viljandi FC Levadia Tallinn
Estonian national team
2000 UEFA Euro qualifying
Estonian Footballer of the Year
Andres Oper

The 1999 season was the eighth full year of competitive football (soccer) in Estonia since gaining independence from the Soviet Union on 20 August 1991.

1999-05-25

FC Levadia Tallinn	3–2	JK Viljandi Tulevik
O'Konnel-Bronin 19' Gussev 51' Krõlov 75'		Ustritski 15' Allas 68'

Sportland Arena
Valga

Attendance: 500

Date	Venue	Opponents	Score	Comp	Estonia scorers	Fixture
1999-01-18	Ramat Gan Stadium Ramat Gan	Israel	7 – 0	F[1]		—
1999-01-22	Hapoel Umm al-Fahm F.C. Umm al-Fahm	Norway	3 – 3	F	Reim 75' (pen.) Zelinski 82' 89'	—
1999-03-03	Stadionul Dinamo Bucharest	Romania	2 – 3	F		—
1999-03-06	Neo GSZ Stadium Larnaca	Azerbaijan	2 – 2	F	Viikmäe 46' Saviauk 71'	—
1999-03-16	Neo GSZ Stadium Larnaca	Cyprus	1 – 2	F	Zelinski 59' Terehhov 85'	—
1999-03-31	Žalgiris Stadium Vilnius	Lithuania	1 – 2	ECQ[2]	Terehhov 49' 77'	—
1999-06-05	Kadrioru Stadium Tallinn	Czech Republic	0 – 2	ECQ		—
1999-06-09	Kadrioru Stadium Tallinn	Lithuania	1 – 2	ECQ	Oper 8'	—
1999-08-18	Pärnu Kalevi Stadium Pärnu	Armenia	2 – 0	F	Kristal 79' Ustritski 90'	—
1999-09-04	Tórsvøllur Tórshavn	Faroe Islands	0 – 2	ECQ	Reim 88' Piiroja 90'	—
1999-09-08	Kadrioru Stadium Tallinn	Scotland	0 – 0	ECQ		—
1999-10-09	Kadrioru Stadium Tallinn	Bosnia and Herzegovina	1 – 4	ECQ	Oper 4'	—
1999-10-30	Al Jazira Stadium Abu Dhabi	Iraq	1 – 1	F	Mahmoud 27' (o.g.)	—
1999-11-01	Al Jazira Stadium Abu Dhabi	United Arab Emirates	2 – 2	F	Reim 19' (pen.) Oper 38'	—
1999-11-03	Al Jazira Stadium Abu Dhabi	Turkmenistan	1 – 1	F	Viikmäe 47'	—
1999-12-18	Trikala Stadium Trikala	Greece	2 – 2	F	Oper 20' 41'	—

• 1999 season on RSSSF
• RSSSF Historic Results
• RSSSF National Team Results