The pair will cross paths again in the FA Cup as Charlton, fifth in League One, face Tottenham, fourth in the Premier League. Beckham is likely to be in attendance if his loan deal from LA Galaxy is completed in time, and Dailly thinks Tottenham's latest coup is further evidence of Redknapp's draw as a manager.
"I'm not surprised. Harry has had a brilliant time since we worked together back then and has gone from strength to strength," he said.
"He has made some tremendous signings. When I signed for West Ham it was very influential that Harry was there and he was the person interested. I had an excellent relationship with him.
"When he phones you it's difficult to turn him down. He has a great personality and he's an intelligent bloke – It's no wonder people want to sign for him. It's why you get people like Paolo di Canio signing for him.
"Harry's teams always play with an expressive nature and players enjoy playing under him."
Charlton's chances of a cup upset at White Hart Lane are further reduced by their lack of a permanent manager after Phil Parkinson was sacked by the club's new owners earlier this week.
Club stalwart Keith Peacock, who previously spent 16 years working as Alan Curbishley's assistant manager, is in temporary charge and Dailly admits the uncertainty is affecting the players.
"There are a lot of disappointed boys in the dressing room," Dailly added. "Phil Parkinson was liked and respected by the players but everybody understood that when we got a new owner then things can change. There's always that possibility.
"In the year and a half since I've been here there have been huge financial constraints put on the club. Everybody has been affected.
"I've never seen anything like it but it's probably happening more and more these days with clubs getting themselves into financial problems."
Peacock, who incidentally shares his birthday with Beckham, admits he does not know who is in line to take over at The Valley.
He said: "I haven't been given any indication on that they just asked me to take charge against Tottenham. My remit is this one game."