Celtic were left to rue their mistakes and missed chances as they somehow came out the wrong side of a five goal thriller at Northolme.
Goals from Jonathan Ustabasi and Charley Doyle were not enough as a brace from Reco Fyfe and a goal from Martyn Woolford sealed a victory for the hosts.
Celtic started the better side and looked to test Thomas Jackson early on. After five minutes, Nic Evangelinos saw an effort fly just over after a promising drive forwards.
Just moments later, Celtic had a superb chance to take the lead. Kallum Mantack played an incisive pass forwards to find Ustabasi, he turned but fired just past the far post.
Celticâ€™s pressure eventually paid off and on 13 minutes Ustabasi put Celtic ahead. After gliding past a couple of challenges, Celticâ€™s number seven took aim and from 20 yards he sent a rocket into the top corner.
AJ Greaves had a chance at the other end but it was all Celtic during the opening 25 minutes. Evangelinos was able to play a neat ball into the path of Lewis Salmon who from a tight angle forced Jackson into a smart save.
Scott Sephton and Evangelinos saw headers fall just over the bar before the hosts equalised with their first real chance of the half on 28 minutes.
Lewis Dennison played a cross in from the right, Woolford managed to get in between Celticâ€™s centre halves and he prodded the ball home.
It went from bad to worse for Celtic as Trinity took the lead on 37 minutes.
A back pass from Ustabasi was just too short and Reco Fyfe latched onto the ball and fired the ball around Tom Stewart.
Just 60 seconds later and Celtic gifted the home side another goal. A shot from the right was parried by Stewart, Celticâ€™s defence had the chance too clear but Fyfe was alert to the loose ball and he tapped the ball in from yards out.
Celtic werenâ€™t ready to give up though and Doyle scored a second for Celtic just before the break. Ustabasi sent in a deep cross, Doyle rose highest and powered a header across goal and into the right hand corner.
Celtic started the second half in search of an equalising goal. Shortly after the restart, Ustabasi played a one two with Evangelinos, the former cut inside but could only hit the side netting.
Mid-way through the half and Ustabasi saw a header fly across goal after a pacey cross by Evangelinos, with the two forwards linking up well throughout the game.
Krisel Prifti was introduced as Celtic ramped up the pressure but it just wasnâ€™t happening for The Celts who had so many opportunities but just couldnâ€™t convert.
Two of those chances came with 15 minutes to go. Callum Harris and Doyle both saw efforts from just inside the area put behind for corners as the home side threw everything in the way to protect their lead.
One of those resulting corners saw Doyle unmarked, almost central to goal he sent a header narrowly wide.
Celtic gave it a real go in the final 10 minutes. Substitute Prifti raced down the right flank, he cut the ball back for Evangelinos who saw his effort saved well by the keeper.
Evangelinos had another go with minutes to go but his effort was over the bar.
The home side managed to see out the game and despite playing five additional minutes at the end of the half, it wasnâ€™t to be Celticâ€™s night.