There was a vocal crowd at the Caledonian Grounds to see two of Dunedin's big guns go head to head in the country's premier knockout competition.
The teams have a rich rivalry and play with an intensity and competitiveness that is unparallelled locally.
Caversham started strongly with a couple of opportunities falling to Fleming in the opening minutes.
It also had the booming long, flat throw-ins of defender Sam Cosgrave as a weapon, with the tiny Caledonian sidelines unable to prevent him from hoisting the ball towards the Technical six-yard box.
Caversham's early pressure paid off in the 20th minute when right winger Ben Wade swung in a fantastic cross for Fleming to powerfully head past Tom Batty. It gave Caversham a 1-0 lead.
Conceding the goal seemed to wake Technical up from its sluggish start, and Caversham keeper Liam Little was called into action for a couple of saves.
Technical, however, was rocked in the 35th minute when Caversham doubled its lead.
The ball found its way through a host of players just inside the Technical box before falling to Lewis Jackson, who squared it across to Fleming to finish from close range.
Technical started the second half well, with midfielders Tim McLennan and Ben Allan getting on the ball more often, and it also made a couple of attacking substitutions to try to get back into the match.
Perseverance paid off in the 65th minute when it was awarded a penalty which divided opinion in the grandstand and on the sideline.
Cam Higgins calmly slotted the spot kick to get his side within a goal of Caversham.
Technical, desperate to find an equaliser, had a couple of late corners and even goalkeeper Batty was thrust forward.
It had a chance in the final minute that fell to defender Andrew Douglas, but his left-foot effort flew over the bar.
Queenstown Rovers was the other Southern team to advance in the Chatham Cup with a 3-1 win over Gore Wanderers in Queenstown.
The home side's scorers were Niall Malone, Jan Kumar, and Matt Cordelle.
Caversham and Queenstown will now have their names drawn along with Christchurch sides Cashmere Technical and Universities AFC to determine the regional round-of-16 fixtures, with the subsequent winners then into the national quarterfinal draw.
Earlier, at Logan Park, the Roslyn Wakari women's side came up against University Premiers in a keenly contested Women's Knockout Cup match.
The match was goalless until the final minute when Jessie Clark-Grant scrambled the ball into the net from a free kick, to send Roslyn into the national quarterfinals in which it is expecting to face a star-studded Cashmere Technical team from Christchurch.
There were two men's Football South premier league matches played on Saturday.
Green Island edged Northern 2-1 at Forrester Park, with a 77th-minute own goal proving the difference after Kieran Stephenson and Shaun Richards had both scored in the first half.
At Logan Park, University had a player sent off in the first half and saw Mosgiel score three goals before the halftime through Matt Kelly, Callum Flaws, and Regan Coldicott.
In the second half, University's Henry Flood scored a stunning 45m consolation goal after spotting the keeper off his line.
Evergreen Mosgiel striker Phil Kelly came on as a substitute to score for a 4-1 victory.
- Morgan Jarvis
