Lena Krasnoroutskaya (Rus) v Conchita Martinez (Spa)
Krasnoroutskaya: Age 17; Seeding n/a; World ranking: 37
Martinez: Age 29; Seeding 19; World ranking: 20
This is a contest between an up and coming player and a past champion coming to the end of her career - Krasnoroutskaya is one of two unseeded players through to the last 16.
She lost in the first round of her five previous Grand Slams but enjoyed an extraordinary run through qualification to reach the quarter-finals at the French Open.
Conchita should find a way to overcome the Russian because of her experience on grass.
Anke Huber (Ger) v Justine Henin (Bel)
Huber: Age: 26; Seeding: 18; World ranking: 21
Henin: Age: 19; Seeding: 8; World ranking: 9
A close one to call. One of the few women players with a single-handed backhand, Henin can seemingly adapt her game to any surface.
She has won three ATP titles this year, got to the French Open semi-finals but struggled against Dutch qualifier Kristie Boogert in the second round at Wimbledon.
She bounced back after being a set and 1-4 down but still may just edge this one.
Jennifer Capriati (USA) v Sandrine Testud (Fra)
Capriati: Age: 25; Seeding: 4; World ranking: 4
Testud : Age: 29; Seeding: 15; World ranking: 19
A danger match for Capriati. Testud has had some big scalps, including Monica Seles a few years ago.
She has a beautiful backhand and has beaten virtually all the top players except Hingis.
Capriati has not yet completely found her rhythm and if she does not show enough respect to Sandrine, Jennifer could go out.
Magdalena Maleeva (Bul) v Serena Williams (USA)
Maleeva: Age: 26; Seeding: 12; World ranking: 14
Williams: Age: 19; Seeding: 5; World ranking: 5
Serena has the weapons to win comfortably but needs to stop her mind from wandering.
We were used to Magdalena being an obstacle at all the top events. She is a regular quarter or semi-finalist, and has come back strongly after a number of injuries.
She has a chance but it's all down to Serena. If she has one of her erratic days - be prepared for a shock.
Kim Clijsters (Bel) v Meghann Shaughnessy (USA)
Clijsters: Age: 18; Seeding: 7; World ranking: 7
Shaughnessy: Age: 22; Seeding: 17; World ranking: 18
Clijsters has to fancy her chances in this match.
Meghann is having a great year and did well to beat Amanda Coetzer in the third round, but is unlikely to bother Clijsters.
Kim has the better record, having been to the quarter-final two years ago and reaching this year's French Open final.
She also seems to benefit a lot from her relationship with Lleyton Hewitt - she has the right mixture of toughness, politeness and common sense and I have a really good feeling for her for the future.
Jelena Dokic (Yug) v Lindsay Davenport (USA)
Dokic: Age: 18; Seeding: 14; World ranking: 16
Davenport: Age: 25; Seeding: 3; World ranking: 3
I am going to go out on a limb and say Jelena will win because she is so hungry and has such a terrific record on grass.
The pair met at the Australian Open where Jelena lost in three sets.
Despite her happiness not having a taxi after her third round match at Wimbledon, she should be totally focused on this match.
She won her first tour title recently, the Italian Open, and unless Lindsay is at the top of her game, Jelena will punish her.
Tamarine Tanasugarn (Tha) v Nathalie Tauziat (Fra)
Tanasugarn: Age: 24; Seeding: 31; World ranking: 31
Tauziat: Age: 33; Seeding: 9; World ranking: 10
This is a battle of minds. These two have played each other twice on grass and both of them have lost from being match point up.
Tauziat is the better pressure player - she has appeared 16 times at the All England Club and was beaten in the 1998 final.
That will give her an edge and she has said this is her last Wimbledon so she will want to go out on a high.
Nadia Petrova (Rus) v Venus Williams (USA)
Petrova: Age: 19; Seeding: n/a; World ranking: 42
Williams: Age: 21; Seeding: 2; World ranking: 2
Nadia is one of a crop of very talented young Russian players.
She will struggle to cope with Venus' power but she knows this is a big opportunity and I expect her to go after it.
Venus is looking like a champion and is improving fast. I backed Venus to win before the start of the tournament and I see no reason to change that now.