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The Highlanders had levelled the scores at 31-31 with a try by Japanese international Fumiaki Tanaka in the final minute of normal time.
But the Reds regrouped and scored the clinching try through number eight Jake Schatz, following 18 phases, two and a half minutes after the siren.
It was a see-sawing match of nine tries, with the Reds leading 21-0 at halftime only for the Highlanders to fight their way back to draw level, crowned by Reds' clinching try.
It was a fitting victory for Wallabies scrum-half Will Genia, who was playing in his 100th match for the Reds and was at the heart of most of their attacks.
Genia provided the kicks which led to tries to Rod Davies and Dom Shipperley in the first half and gave the final pass for Schatz's second and winning try after the siren.
Genia was given the final kick to convert Schatz's try.
The win ended the Reds' six-match losing run in Super Rugby and lifted them off the bottom of the standings.
The Highlanders got two points out of the defeat, a losing bonus point and for scoring four tries to move above Western Force in the top six positions.
The Reds played some of their best rugby in a troubled season with three converted tries in the opening 34 minutes through Curtis Browning, Davies and Shipperley with Mike Harris deadly accurate with the conversions.
But the Highlanders hit back in the second half with tries by Lima Sopoaga, Richard Buckman and Patrick Osborne with Schatz scoring his first try off a Reds pushover scrum.
Replacement scrum-half Tanaka looked to have rescued a draw for the Highlanders when he dived over a ruck for a converted try only to set up the Reds' last-gasp winning try.
"It's good to win again, it's been a while," Reds skipper James Horwill said.
"We made it hard for ourselves in the second half but found a way to win in the end."
Scorers:Reds: 38 - Tries: Curtis Browning, Rod Davies, Dom Shipperley, Jake Schatz; Conversions: Mike Harris (4), Will Genia; Penalty: Harris
Highlanders: 31 - Tries: Lima Sopoaga, Richard Buckman, Patrick Osborne, Fumiaki Tanaka; Conversions: Sopoaga (2), Hayden Parker (2); Penalty: Parker
Teams:
Reds:
15 Mike Harris, 14 Dom Shipperley, 13 Ben Tapuai, 12 Anthony Fainga'a, 11 Rod Davies, 10 Ben Lucas, 9 Will Genia, 8 Jake Schatz, 7 Beau Robinson, 6 Curtis Browning, 5 James Horwill (captain), 4 Rob Simmons, 3 Greg Holmes, 2 James Hanson, 1 James Slipper
Substitutes: 16 Andrew Ready, 17 Albert Anae, 18 Sef Faagase, 19 Dave McDuling, 20 Liam Gill, 21 Nick Frisby, 22 Samu Kerevi, 23 Jamie-Jerry Taulagi
Highlanders:
15 Ben Smith, 14 Richard Buckman, 13 Malakai Fekitoa, 12 Shaun Treeby, 11 Patrick Osborne, 10 Lima Sopoaga, 9 Aaron Smith, 8 Nasi Manu, 7 Shane Christie, 6 Gareth Evans, 5 Joe Wheeler, 4 Jarrad Hoeata, 3 Ma'afu Fia, 2 Liam Coltman, 1 Kane Hames
Substitutes: 16 Ged Robinson, 17 Matias Diaz, 18 Chris King, 19 Tom Franklin, 20 Elliot Dixon, 21 Fumiaki Tanaka, 22 Hayden Parker, 23 Phil Burleigh
