Ex-Blues Ray Crawford and Gary Roberts are both delighted that Monday’s FA Cup third round draw paired Town with Portsmouth at Portman Road.
Blues all-time top scorer Crawford, 79, who began his career with hometown club Pompey and returned to the area at the end of his playing days, believes the League Two side have a chance of creating an upset.
"I think it is a tremendous draw,’ he told the Portsmouth News. "Going to Ipswich gives you a good playing surface, while they are not doing particularly well at home, they are doing better on their travels.
"I am looking forward to Pompey getting a result up there. I don’t know about a win, but I think we can easily get a replay.
"I was up there a couple of weeks ago when they played Wolves and they huff and puff at the moment. One minute they look good and the next look very vulnerable at the back.
"Daryl Murphy doesn’t look anything like he was last year when banging the goals in for fun.
"David McGoldrick is injured and he makes them tick, he’s a clever player. He plays up front but drops off and gets the ball and feeds it through. Hopefully he will be out when we play them!”
Crawford was a member of Sir Alf Ramsey’s side which won the Second and First Divisions in 1960/61 and 1961/62 and returned for a second spell at Portman Road to help Bill McGarry’s team to the Second Division title in 1967/68.
In total, Town’s first-ever England international scored 227 goals in 353 games for the Blues.
Roberts, 31, was with Town between October 2006 and July 2008, initially on loan from Accrington Stanley, and went on to make 45 starts and 14 sub appearances for Town, scoring four goals.
The winger, who has been sidelined since the end of October with an ankle problem having moved to Fratton Park from Chesterfield in the summer, is looking forward to catching up with a few faces from his time at the club.
"I haven’t been back there since I left a good few years ago and it will be nice to return and see a few people,” he told Portsmouth’s official website.
"They’re a big club with a lot of history and nobody will expect much from us, but hopefully we can go there and win the tie.
"I’m sure they’ll be on the front foot and looking to beat us, which is something we don’t experience very often in League Two.
"That will probably suit us, although it’s still going to be a very tricky game because they’re a strong Championship team.
"We’ve got some big games before going there, however, and play a lot of sides who are around us in the table over Christmas.”
Roberts says he’s not too far away from a return to action: "I want to be back as quickly as possible. The physio’s being a bit tight and not letting me kick on as much as I’d like to.
"But that’s his job and if he can ensure that I stay on the pitch for the rest of the season then I’m happy to wait a bit longer.”
The Portsmouth squad also includes former Town keeper Brian Murphy, while one-time academy striker Caolan Lavery is currently on loan at Fratton Park from Sheffield Wednesday.
Blues defender Matt Clarke’s half-season loan with Pompey is due to end on Sunday 3rd January - third round ties are due to be played the following weekend - but wouldn’t be permitted to face his parent club in any case.