| Player | Opponent Ranking | Tournament | Opponent | Result | Score | Surface | Eventually lost in which round, if won the opening match |
|---|---|---|---|---|---|---|---|
| Borg | NA | Valencia, Spain | Corrado Barazzutti (ITA) | Won | 6-4, 6-2 | Outdoor Clay | Second round |
| Sampras | 105 | Philadelphia, PA, U.S.A | Sammy Giammalva Jr. (USA) | Lost | 4-6, 3-6 | Indoor Carpet | Lost in opening round |
| Lendl | NA | Roland Garros, France | Jose-Luis Clerc (ARG) | Lost | 3-6, 0-6, 3-6 | Outdoor Clay | Lost in opening round |
| Agassi | NA | La Quinta, CA, U.S.A | John Austin (USA) | Won | 6-4, 6-2 | Outdoor Hard | Second round |
| Connors | NA | NA | NA | NA | NA | NA | NA |
| Federer | 88 | Gstaad, Switzerland | Lucas Arnold Ker (ARG) | Lost | 4-6, 4-6 | Outdoor Clay | Lost in opening round |
| Nadal | 731 | Spain F10, Madrid | Guillermo Platel (ESP) | Lost | 6-2, 5-7, 2-6 | Outdoor Hard | Lost in opening round |
| Djokovic | 664 | Germany F1A, Munich, Germany. | Alex Radulescu (GER) | Lost | 5-7, 6-7(5) | Indoor Hard | Lost opening match |