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He is the top scorer in the league, with 12 goals, and was part of a side which racked up a commanding 7-2 victory over Waitakere last weekend.
Jackson (26) played for Southern United — or Otago United as it was known back then — for many years before he shifted up to Wellington in 2015.
Jackson says he enjoyed playing against Southern United, though it was not always easy.
"It’s definitely interesting. You enjoy it obviously playing against guys that you know quite well. But I’m still a Southern United supporter. I really want them to win games," he said.
"But the games I play against them I do not want to lose against them. Those are the two games of the season I definitely do not want to lose. But I genuinely do believe they are one of the better teams in the league but maybe they are just not great in front of goal, converting those chances."
Jackson scored a hat trick last time the teams clashed in December in the capital and will look to continue that goal-scoring form.
Indeed Team Wellington does not appear to be having any problems in front of goal judging by a seven-goal onslaught last week after being down 2-0 to Waitakere.
"I think that has been brewing for the last few weeks ... but we’ve got guys in the team who have got goals in them."
Jackson said new Team Wellington boss Jose Figueira had made a real difference to his game.
"He just goes that extra mile and I’ve learnt a lot off him."
Jackson was one of many former Southern United players who were playing for other teams in the premiership. The likes of Joel Stevens, Tristan Pratley and Cam Howieson come to mind. If Southern United could get them all back it would have a formidable side.
Jackson said it was not quite that simple.‘‘It is not just about moving away to get more football. It is more about jobs, the lifestyle and wanting to do something different.
"Jackson worked for ACC in Wellington as a recruitment administrator and is engaged to former Dunedin woman Morgan O’Fee. They have set a wedding date in November. Jackson had a trial with the Phoenix a few years ago but nothing eventuated. He was not waiting for another opportunity to come along.
"That ship has sailed I reckon. Don’t get me wrong. If someone came along and made me an offer I wouldn’t say no. But things have to fall for you. I would never say never, but not at the moment."
Jackson was hoping Team Wellington would qualify for the playoffs and then go into O League playoffs. He would have a short break before playing winter football in Wellington.
His younger brother, Lewis, had trained with Team Wellington for the season, without playing any games, and had signed for Miramar to play in winter.
Tom Jackson’s side was leading the league but that was short-lived with Auckland City beating Hamilton Wanderers in a catch-up game last Wednesday to go top of the league on goal difference.
Southern United will take on Auckland City next Wednesday in a catch-up game.
Southern United goalkeeper Liam Little is out with a back injury, which has been bothering him for some time and he is replaced by Josh Djikstra. Sam Collier misses the match with a hamstring injury.
On the plus side, Danny Ledwith and Andy Mulligan come back into the team after serving suspensions.
The match is at Rugby Park Stadium in Invercargill, the second game to be played in the south this season.
Southern United lost to Auckland City 1-0 in Invercargill last November.
Invercargill, tomorrow, 3pm
Southern United: Josh Djikstra, Sam Cosgrave, Conor O’Keefe, Stephen Last, Hamish Cotter, Harley Rodeka, Ross Howard, Danny Ledwith, Eric Molloy, Danny Furlong, Andy Mulligan. Substitutes: Riley Anderton, Ben Wade, Michael Hogan, Andrew Ridden, Tom Stevens.
Team Wellington (likely): Scott Basalaj, Justin Gulley, Guillermo Moretti, Bill Robertson, Taylor Schrijvers, Leonardo Villa, Tom Jackson, Nathanael Hailemariam, Andy Bevin, Nick Edginton, Joel Stevens, Ben Harris, Nicolas Zambrano, Josh Margetts, Nico Kirwan, James McPeake.