Annan Athletic 1 Carlisle United 2: Carlisle got their pre-season campaign off to a winning start after a late fightback at Annan.
Trialist Stephen Walker hit a last-gasp winner after Jack Armer had cancelled out Josh Galloway's early Annan opener.
It came on a night Carlisle handed Sam Lavelle a first outing, while another trialist, goalkeeper Dan Langley, featured in the second half.
Carlisle's new defensive signing Lavelle was in their first half line-up against Peter Murphy's Annan, with fellow Friday arrival Dylan McGeouch not involved as he trained back at Brunton Park.
Simpson also handed a start to youth team prospect Romeo Park, as the manager sent his side out for the first time since May's play-off final at Wembley.
United began on the front foot and Jordan Gibson twice went close in the opening stages, first shooting just wide from outside the box, then dened from closer range by keeper Greg Fleming.
But Annan then broke and drew first blood when former Blues youth product Galloway got behind United's defence on the break, and finished confidently past Tomas Holy.
Murphy's side were a danger through the line-leading of Tommy Goss and the running of Galloway, Aidan Smith and Chris Johnston, and forced a number of corners.
One of them fell to Goss in space at the back post but he screwed his shot wide, while Johnston forced United into a last-ditch block as he cut in from the right.
At the United back, Lavelle was a vocal presence on the right of the central defensive three, while Carlisle looked to find a way back, Gibson testing Fleming with a cross, Jack Robinson seeing a good delivery go unrewarded and Park a willing worker up front alongside Joe Garner.
Lavelle tried his luck from 30 yards and saw his shot spin over the top right corner of Fleming's goal, while Max Kilsby, facing his former loan club, tested Fleming with a low drive from similar distance.
Annan, though, could be pleased with an accomplished first half showing in which Josh Dixon, facing his former club, put in an impressive and controlled midfield display.
United then sent out a different XI for the second half, featuring two trialists - understood to be ex-Newcastle keeper Langley and former Middlesbrough attacker Walker, neither man named officially by the Blues.
Ben Barclay and Alfie McCalmont were among those also to get outings, their first since signing permanent deals, with Kai Nugent also getting a first appearance since turning pro.
Langley was called into action early to save a Johnston drive before United upped things in the Annan half, pressing well and forcing the hosts back.
A McCalmont cross was headed just wide by Ryan Edmondson and, after the Blues had just about managed to deal with a Galloway cross at the other end, Ben Barclay warmed Fleming's gloves with a well-struck shot.
United almost levelled when a good move ended with McCalmont taking aim, Fleming saving well - and then the Annan No1 brilliantly kept out an Edmondson header from Moxon's corner.
Home sub Benjamin Luissint helped the hosts gain a fresh foothold and he almost set up Goss, before Moxon was denied from the right for United.
Annan then replaced Dixon with Lewis Bell, the ex-Blues winger who is on trial, and Carlisle came close when an attempted rabona from McCalmont was cleared as far as Jayden Harris, who rifled just wide.
The bright Nugent, combining with trialist Walker on the right, almost opened something up, while United's other trialist, Langley, was at full stretch to punch clear a dangerous cross.
Annan fielded a number of youngsters in the second half and Carlisle should then have levelled in the 78th minute, as they broke from a home free-kick, but Edmondson headed over an empty net.
But their pressure finally told when Edmondson nodded down a Barclay cross and Armer arrived to prod it home.
And United, with Jon Mellish a constant late presence in their attacking, struck again with their final attack, Nugent setting up Walker from close range.
Annan: Fleming, Hooper, Trialist, Trialist, Douglas, Swinglehurst, Galloway, Docherty, Smith, Goss, Johnston. Subs: Mitchell, Trialist, Trialist, Trialist, Trialist, Trialist, Luissint, Trialist, Trialist.
United (first half): Holy, Lavelle, Huntington, Ellis, Robinson, Kilsby, Guy, Charters, Gibson, Park, Garner. (second half) Trialist, Armer, Whelan, Barclay, Mellish, Harris, Nugent, Moxon, McCalmont, Trialist, Edmondson. Subs: Allan, Fitzpatrick, Swinburn.
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