Looking to make amends for a deflating first-round defeat in the Canadian Open against the Ukraine's Alexandr Dolgopolov earlier in the week, the world's 21st-ranked Anderson could slip from the firing pan into the fire with a first round draw in Cincinnati pitting him against the revitilised, 35-year-old 11th seeded Tommy Haas.
An additional motivation for Anderson, however, is that if he beats Haas and goes on to make it to the third round, he could satisfy a long-standing ambition to play legendary, 17 grand slam winner Roger Federer for the first time.
In a curious quirk of fate, Anderson has not played against Federer even once since joining the ATP professional circuit in 2007.
And this would not be a bad time to finally face Federer either, with the iconic legend's form wavering while his ranking has slipped to fifth in the world, with recent defeats against players rated 50th and 115th suggesting it could deteriorate even further for the Cincinnati defending champion.
Anderson would need to beat Haas and either Marcel Granollers or Lukas Rosol in the second round before thinking of a Federer match-up - with the Swiss maestro having to beat tough opposition in Mardy Fish or Philipp Kohlschreiber as well in the second round.
In the meantime, the South African Davis Cup team for the relegation-saving Euro-Africa Group One tie against Slovenia next month is due to be announced on Wednesday without the controversially unavailable Anderson and the injured Izak van der Merwe leaving team captain John-Laffnie de Jager with some acute selection headaches.