Dundee United pair William Edjenguele and Jordie Briels came through their returns from injury unscathed as the Development side lost out 2-1 to Hearts.
Central defender Edjenguele has been missing for the past two months and played an hour on Tuesday night at the Oriam in Edinburgh.
Dutch midfielder Jordie Briels, meanwhile, has been out for even longer with his last first-team appearance coming way back in October in a 2-0 loss to Livingston.
He came through a scheduled 45 minutes for the U/20s as he continues his battle to regain his fitness.
The returning pair couldn’t help get the young Tangerines off the foot of the table, however, as the Jambos came out on top.
Goalkeeper Deniz was rarely troubled by the home side until they took the lead through a trialist on 27 minutes.
After the break, Deniz was on hand to keep out a Calum Morrison drive, tipping it over the bar.
After this, United started to make more of the running and Luc Bollan’s header forced a fine save from the Hearts goalkeeper.
After the break, Logan Chalmers dragged a shot wide before substitute Gav Ritchie cleared a Dario Zanatta effort off the line before Louis Appere got United level with 10 minutes remaining.
Idris Kadded, though, earned himself a second booking in the aftermath of that strike.
Against 10 men, Hearts grabbed a late winner with Aidan Keena finding the corner with three minutes to go.
The defeat leaves the young Tangerines in 14th spot at the bottom of the table, level on points with Kilmarnock.