David Templeton enjoyed a happier trip to Galabank as Rangers recorded their 11th consecutive Irn-Bru Third Division victory.
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The winger, who was carried off with ankle ligament damage when Rangers drew 0-0 in Annan in September, opened the scoring on Wednesday and helped round it off when his 25-yard strike was deflected home by defender Harry Monaghan.
Robbie Crawford had earlier put Rangers back in front after Ally Love brought Annan level before the break with an almost identical goal to the opener, with his cross sailing straight in.
Rangers did suffer another serious-looking injury though when Darren Cole was stretchered off on his first start of the season.
Rangers had made three changes before the game with skipper Lee McCulloch missing out with an ankle problem.
Cole came in at right-back, Francisco Sandaza started as a lone central striker and Andrew Little came in on the right flank.
Emilson Cribari, who recently returned from injury, was not risked on the artificial surface.
Templeton - who has since modified his footwear for non-grass surfaces - started and Little had early shots on target but Alex Mitchell held both and Rangers midfielder Ian Black was booked for a late tackle on Chris Jardine in a scrappy opening phase.
Michael Daly had the first chance at the other end when he shot into the side netting from a tight angle with the ball taking a deflection off a Rangers defender.
Rangers took the lead in the 26th minute shortly after Cole's long ball over the top of the home defence put Sandaza through, and after Mitchell had pushed the Spaniard's shot away from goal.
Templeton, who scored twice against Annan at Ibrox last month, retrieved the ball on the left wing and sliced a left-footed cross that beat Mitchell and nestled in the far corner.
Sandaza missed a glorious chance to open his Rangers account when Templeton's inswinging corner found him unmarked four yards out with the goal gaping.
However, the Spaniard's downward header bounced off the surface and up on to the bar and away.
Annan were level in the 35th minute. Love got the better of Cole on the left wing and sent over a left-footed cross from near the touchline that sailed over Neil Alexander's head.
Sandaza missed a more difficult chance when he stretched to hit Cole's far-post cross high and wide.
Black had a shot saved early in the second half and Crawford had several efforts miss the target but Rangers were being made to work hard for any sight of goal.
Rangers defender Ross Perry was booked late tackle on Jack Steele, who was quickly followed into Stephen Finnie's notepad by Daly for an off-the-ball shove on the Rangers defender.
Cole pulled up after making a forward run and was carried off on a stretcher in the 56th minute with Sebastien Faure coming on.
Love soon had a shooting chance but sent a weak effort straight at Alexander.
Rangers went ahead in the 63rd minute. Templeton's cross was only half headed clear and Crawford shot into the bottom corner from 12 yards.
Annan sub Blair Currie had a shot blocked and then failed to get enough contact on Monaghan's header to beat Alexander from close range.
And the game went beyond the hosts in the 83rd minute when Templeton's 25-yard strike took a major deflection off Monaghan and flew high into the net.