When his team-mates are facing University at Tonga Park, Jackson will be in the Wellington squad preparing to face AS Tefana in Suva this weekend.
The O-League group stage starts tomorrow and Wellington faces further games on April 15 (against Heraki United) and April 17 (Tafea FC). If Wellington qualifies, the semifinal is on April 21, followed by the final on April 26.
All the group matches featuring New Zealand representatives Auckland City and Wellington will screen live on Sky Sport, which has also picked up the semifinals and final.
It has been an impressive year for Jackson, who tied with Tyler Boyd for the ASB Premiership golden boot after the regular season. Meritoriously, Jackson's effort was for the bottom team, for which he scored exactly half the goals.
In recognition of his scintillating form, Jackson won Southern's three major player awards - player of the year, players' player and golden boot.
In his shadow, brother Lewis won the Southern youth team's players' player and golden boot awards, to give the Jackson family an almost clean sweep of awards.
Goalkeeper Josh Dijkstra was named the youth team's player of the year, and Andrew Ridden was awarded the senior team's young player of the year award.
Caversham coach Tim Horner said Tom Jackson's haul was ''well deserved'' and the South Dunedin club was also delighted to see Lewis Jackson and Ridden claim honours.
Caversham aims to win yet another Football South Premier League title this year, but could face stiff competition from Dunedin Technical, the volatile University side, and coach Andrew Brooks' rebuilt Mosgiel side.
Caversham faces the students at Tonga Park today and University coach Darren Hart hopes all his squad will be back from Easter holidays.
Mosgiel faces its most demanding test so far at Memorial Park, where it hosts a Technical team scoring goals for fun - understandably, with former multiple golden boot winner Aaron Burgess at the helm.
Technical has scored 10 goals in two games and conceded just two, so the game should be well contested.
At Ellis Park, Roslyn-Wakari faces Northern, both teams struggling to find form. Green Island racked up five goals last week against Northern, but has the bye.
Tomorrow, the women's league starts with an interesting tussle between University and a Queenstown side coached by Brazilian Daniel Bocatios at Logan Park.
At Culling Park, Dunedin Technical plays old rival Roslyn-Wakari. Wayne van Gorp is rebuilding his Roslyn side, and the Technical women, under Graeme Smaill, are aiming to win another title.
''A few new faces in the team this year but all are looking forward to a strong and competitive season,'' Smaill said.
