1) Maria Bueno vs Monica Seles: This is a very intriguing matchup, as you have the master of spin and grace, though not necessarily known for her mental fortitude versus the queen of pace and awkwardness, with the mental tenacity of a pitbull. I would give Bueno the edge on grass because I could see her giving Seles fits with her ability to mix things up, however,I think that Seles' return would give her the edge on hard court and a grass court. I would pick Seles to win the majority of their matchups but Bueno would always be dangerous.
2) Margaret Court vs Venus Williams: I give the edge to Court. Venus just has more weaknesses to exploit, primarily the forehand and the second serve. Venus has the better speed, but Mags was no slouch in that department. I think that Court's stronger second serve would be the key in this match.
3) Ann Haydon-Jones vs Chris Evert: At first I would have picked Chrissie hands down, before recalling that Evert much preferred to play serve and volleyers to baseliners, especially good baseliners like Nancy Richey, Austin, Graf etc. Jones was definitely in the Austin/Richey category and those two gave her more fits than anyone this side of Nav. Add in Jones lefthandedness and I think we got a pretty even match. I would pick Chrissie to win this one about 6 out of 10 times.
4) Lesley Turner vs Aranxta Sanchez-Vicario: I think Turner's more sophisticated baseline game would have carried the day most of the time against Arantxa.
5) Billie Jean King vs Serena Williams: Serena, BJK might get a set based on sheer court sense, but at the end of the day Serena's greatness would get the best of BJK.
6) Virginia Wade vs Amelie Mauresmo: The languid Frenchwoman versus the tightly wound English maid? I would give it to "Our Ginny" based on sheer guts.
7) Evonne Goolagong vs Gabriela Sabatini: The battle of the second serves? The battle of the mental midgets? I would pick Gooly in this one because I find her to be more multidimensional and quick than Gaby. The more I think about this one the more I realize that everything Gaby did Gooly did better.