Our men’s legends make their 2017 New Haven debut on Day 5 as Connecticut’s own James Blake takes on 1989 French Open champion Michael Chang on Thursday night.
It also marks the 17th Connecticut Open Family Classic, which provides families spirited competition and the chance to share the stage with some of the top women players.
Here are our three matches to catch on Day 5:
 Agnieszka Radwanska (POL) v  Peng Shuai (CHN)
The defending champion hit the ground running in her 2017 New Haven debut holding off a late fightback from Eugenie Bouchard to reach the quarter-finals on Tuesday night. Peng, meanwhile, booked her place with a relatively routine win over Australian Open semi-finalist Mirjana Lucic-Baroni. The 10th-ranked Pole and 23rd-ranked Chinese player have split their six career meetings with Peng claiming their past two clashes, including on hard courts at Indian Wells this year. “I lost to both of them this year so that for sure is going to be a good chance to get revenge,” Radwanska said of facing Peng or Lucic-Baroni.
 Dominika Cibulkova (SVK) v  Anastasia Pavlyuchenkova (RUS)
A confidence-boosting victory over gutsy Frenchwoman Alize Cornet on Wednesday night had Dominika Cibulkova hailing it the kind of form that carried her to the season-ending WTA Finals title last season. Russia’s Anastasia Pavlyuchenkova was also impressive in her dismissal of former world No.6 Carla Suarez Navarro on Wednesday. Now the familiar rivals square off for a semi-final berth with the Slovak holding a 5-3 advantage. “Always against [Pavlyuchenkova] it’s really tough,” Cibulkova said. “She plays aggressive, goes for her shots. I just have to stick in there and wait for a good moment.”
Daria Gavrilova (AUS) v Kirsten Flipkens (BEL)
The spritely Aussie had an extra spring in her step after she ground out a sapping win over Timea Babos on Tuesday. It put the world No.26 in the box seat to reach her second semi-final of the season knowing her opponent would be a qualifier – either world No.76 Kirsten Flipkens or 127th-ranked Ana Bogdan. Former Wimbledon semi-finalist Flipkens sliced and net-charged her way past Bogdan to reach her second quarter-final of the season. The Belgian beat Gavrilova in their only prior encounter, but it was five years ago on grass at ’s-Hertogenbosch. “She's a tough opponent, she’s going to be hanging in there, playing really well the last couple of days, so I'm just looking forward to going out there and playing her,” Flipkens said.