His wish was not granted, however, and on Sunday his new team line up against his old one at Wembley Stadium for a place in the final.
"I was pleased they (Portsmouth) got through but I really didn't want to draw them. I was hoping to draw Aston Villa.
"I'm not saying that would be an easy game but we wanted to avoid Chelsea and I didn't really want to play Portsmouth," Redknapp told reporters at the Spurs training ground tucked away down a country lane in the leafy Essex suburb of Chigwell on Friday.
Surely, though, facing the team he steered to FA Cup glory in 2008 was a mouth-watering prospect?
"It's another game," he said. "It takes an awful lot to get me very excited. I know a lot of the lads there well," Redknapp added before reeling off the names of several Pompey players including Kanu, who he picked up on a free transfer and went on to score the winner in the final.
Despite Portsmouth's financial problems and impending relegation from the Premier League, Redknapp said he was worried about playing a team who will turn up with little expected of them and without the kind of pressure Spurs face as favourites to reach the final of a competition they last won in 1991.
"I genuinely think they (Portsmouth) are very dangerous," he added. "It's a one-off game and they come in as big underdogs.
"They have got players that can cause us problems. I have got great respect for the manager (Avram Grant) as someone who knows what he's doing."
WORKED TOGETHER
Redknapp and Grant worked together when the Israeli was director of football at Fratton Park and they are friends who sometimes share a bottle of wine together although they have not spoken much in the build-up to the match.
"I had dinner with him last week," said Redknapp. "We've kept out of each other's way this week. We've both had a lot of injuries to contend with. I look forward to seeing him. He's done a terrific job for them."
So what kind of reception does Redknapp expect from the Portsmouth fans on Sunday?
"People got upset when I left because I had done such a good job there," he said. "But it's a Cup semi-final. It's going to be a sunny day. Go and enjoy a good game of football," he urged the fans.
Redknapp looked relaxed in his casual club shirt and tracksuit top as he considered the possibility of another Wembley final - it would be his third in three years after Pompey's FA Cup success and Tottenham's defeat by Manchester United on penalties in last year's League Cup final.
The visit of Arsenal next Wednesday also starts a Premier League spell in which Spurs will also host Chelsea and travel to Manchester United.
"It's nice to be up there at the top looking to try to get into the top four and a Cup final," said Redknapp. "It's a massive week but it's better than being stuck at the bottom in a relegation battle. It's an enjoyable week."
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