The 1938 Estonian Cup (Estonian: Eesti Karikas) was the first season of the Estonian football knockout tournament. 11 teams took part of the competition. In that time there was no penalty shoot-out after extra time. Because of that another final had to be arranged as the first match ended 1–1. In the second match, played on 6 November in Kadriorg Stadium, VS Sport Tallinn narrowly won over Tallinna Jalgpalliklubi, thus becoming the first cup champions of Estonia.

18 September 1938

VS Sport Tallinn	1–1 (a.e.t.)	Tallinna Jalgpalliklubi
Siimenson 8'		Velisto 55'

Kadrioru staadion, Tallinn

Referee: Henrich Paal

6 November 1938

VS Sport Tallinn	2–1 (a.e.t.)	Tallinna Jalgpalliklubi
Brenner 29' Kleesmann 97'		Kastanja-Kastan 25'

Kadrioru staadion, Tallinn

Attendance: 1,000

Referee: Oskar Koni

• Estonian Cup 1938 at RSSSF