| 1969-06-23 | Wimbledon | Grass | R128 | - |  Zeljko Franulovic | - |  Toomas Leius | 7-5 6-8 6-3 7-9 10-8 | H2H | 5 | - | - | - | - | - | - | - |
| 1969-05-26 | Roland Garros | Clay | R128 | - |  Patricio Rodriguez | - | Toomas Leius | 7-5 6-2 5-7 7-5 | H2H | 5 | - | - | - | - | - | - | - |
| 1969-05-23 | Davis Cup EUR QF: URS vs CAN | Clay | RR | - |  Mike Belkin | - | Toomas Leius | 7-9 6-3 4-6 6-2 9-7 | H2H | 5 | - | - | - | - | - | - | - |
| 1969-05-23 | Davis Cup EUR QF: URS vs CAN | Clay | RR | - | Toomas Leius | - |  John Sharpe | 6-4 6-4 6-4 | H2H | 5 | - | - | - | - | - | - | - |
| 1969-05-09 | Davis Cup EUR R1: GRE vs URS | - | RR | - | Toomas Leius | - |  Nicholas Kalogeropoulos | 5-7 3-6 6-4 6-2 4-0 RET | H2H | 5 | - | - | - | - | - | - | - |
| 1969-05-09 | Davis Cup EUR R1: GRE vs URS | - | RR | - | Toomas Leius | - | Periclis Gavrilidis | 6-1 1-6 6-4 6-4 | H2H | 5 | - | - | - | - | - | - | - |
| 1969-06-13 | Davis Cup EUR SF: URS vs ITA | - | RR | - | Toomas Leius | - |  Eugenio Castigliano | 4-6 3-6 6-4 7-5 6-2 | H2H | 5 | - | - | - | - | - | - | - |
| 1969-06-13 | Davis Cup EUR SF: URS vs ITA | - | RR | - | Toomas Leius | - | Nicola Pietrangeli | 6-4 6-4 6-8 6-3 | H2H | 5 | - | - | - | - | - | - | - |
| 1969-07-18 | Davis Cup EUR F: ROU vs URS | Clay | RR | - |  Ilie Nastase | - | Toomas Leius | 4-6 6-3 6-2 6-2 | H2H | 5 | - | - | - | - | - | - | - |
| 1969-07-18 | Davis Cup EUR F: ROU vs URS | Clay | RR | - | Ion Tiriac | - | Toomas Leius | 6-3 6-3 8-6 | H2H | 5 | - | - | - | - | - | - | - |
