Top Spin 4

This one will come through natural progression through the Career mode, but it may take some time - you have to be at Superstar rank before these unlock, so be patient.

Eventually, once you have reached Superstar rank, you will start getting mails inviting you to Dream Matches against any of eight former superstars. You can access these through the Special Events menu.

Be warned - much like the semi-finals and final of Grand Slams are clearly elevated by a difficulty rung (notice how much easier it is to beat Federer in the final of a Masters tournament than the semi or final of a grand slam), Dream Matches are also lifted in difficulty. If you are having trouble with this, drop the difficulty level and it will revert to being a breeze. Dream Matches on the top difficulty level can be extremely tough.

You will definitely get this achievement on route to 'The Greatest' since winning all eight dream matches is one of the requirements for that one.