Stirling struck three sixes and four fours as he scored 56 from just 43 balls helping Ireland make 120 for 7 in their allotted overs.
The 23 year-old took a particular shine to former Irish international Peter Connell, as he smashed 19 from his third over during an opening stand of 49 with skipper William Porterfield (17).
Niall O'Brien was run out for just a single, while Kevin O'Brien and Gary Wilson chipped in with 13 and 21 respectively.
Mohammed Waseem (3-16) was the stand-out performer for the home side.
Max Sorensen and Stuart Thompson (1-7) took early wickets as Wings got off to a poor start, wobbling on 7 for 3, as they attempted to gain their second win over an Associate in 24 hours - having beaten Afghanistan by eight wickets on Friday.
Former Zimbabwean Test player Charles Coventry, who once held the record for the highest score in an ODI - 194 not out against Bangladesh in 2009 - steadied the ship along with Barbados all-rounder Alciendro Holder.
The pair added 55 in 11 overs, before Paul Stirling dismissed Coventry for 36 (31 balls, 1 four, 3 sixes) and from then on Ireland were always firmly in control. Dangerman Alciendro Holder top scored with 41 from 38 balls (2 fours, 2 sixes) before becoming the third of Max Sorensen's (3-9) victims.
Kevin O'Brien bowled superbly at the death, claiming 3 for 19 as Wings were dismissed for 106. It was a day of comebacks, as Niall O'Brien was back behind the stumps for Ireland, taking two catches in an impressive display, while Alex Cusack (1-12) returned from injury to take the final wicket and clinch the 14 run win.
Ireland continue their ICC World Twenty20 preparations with warm-ups against The Netherlands on Tuesday and PNG the following day. Their opening game in the tournament is against Namibia in Abu Dhabi next Friday.
T20 Friendly
At Dubai, Ireland XI beat Wings XI by 14 runs
Ireland XI 120-7 (20 overs, P Stirling 56, G Wilson 21, W Porterfield 17, Waseem 3-16) beat Wings XI 106 all out (19.4 overs, A Holder 41, C Coventry 36, M Sorensen 3-9, K O'Brien 3-19) by 14 runs.