The 28-year old goalkeeper is preparing to take on Sydney FC in a do or die Preliminary Final on Saturday but news that he is likely to sign with the Sky Blues soon must make things feel extremely peculiar.
The ex-Brisbane Roar gloveman is on a short-term deal with the New Zealand club and although he did not confirm the rumours that he was going to sign with Sydney for three years, he did not deny it either.
''No, not really (things being awkward). If it happens that I help knock out my future employers, that's something they might have to take up with me next year," Reddy said.
"Right now I'm a Wellington player, they pay my wages, and there's nothing I'd like better than playing in my first grand final.''
And Sydney coach Vitezslav Lavicka admitted he was a player the club was looking at.
''I've thought about it, I watched their game [against Newcastle Jets] and he did a very good job he has also been good not just in that game but in the last part of the season for Wellington, just like their whole team. It will be interesting to play against him on Saturday, but of course we have a real intention and a big desire to win," the Czech tactician added.