The experienced League Two side made their opportunities count on the evening as a stunning strike from Zebedee Lawson in the first-half, coupled with goals from Arran Kerr and Lewis Stewart either side of the half-time interval, wasn’t enough for the side to retain their grip on the trophy.
Scott Williamson struck the winner for the away side, with the young Gers now shifting their attention to their final three league outings of the campaign with plenty still up for grabs.
The home side dug into their pool of loan players for the last four clash, introducing the likes of Callum Burnside and Calum Adamson.
Goalkeeper Rydnn McGuire and full-back Ashton Scally are involved in the first-team training camp in Spain, facilitating the introduction of Alfie Halliwell, on loan at Albion Rovers, between the posts for this one.
Clyde themselves brought plenty of experience to Milngavie, with their starting lineup underlining their ambitions in the competition.
Indeed, the hosts fashioned the first attempt towards goal inside three minutes when Burnside, who has netted nine times on loan at Alloa Athletic this term, let fly from 30 yards but arrowed wide of the Clyde goal.
However, they suffered an early setback inside seven minutes when too much time and space was afforded to Cuddihy and his effort from distance took a wicked deflection beyond Halliwell.
Rangers sought an immediate response just minutes when neat approach play freed Aiden McCallion in space. He carried the ball the length of the Clyde half, delaying his pass just in time to find Calum Adamson in space whose strike was thwarted by a last-ditch block from Logan Dunachie.
The equaliser arrived with a quarter of an hour on the clock, and it was one which certainly belongs among the finest strikes this season.
Burnside was the architect on the left-hand side when he flashed the ball crossfield towards Lawson, whose first-touch was immaculate, creating a half yard inside the Clyde full-back before he curled a sumptuous finish in off the underside of the crossbar.
But such was the back-and-forth nature of the opening period that parity lasted just seven minutes.
This time it was Cannon who drifted in off the right for the away side and his left-footed effort beat Halliwell despite the goalkeeper getting his left wrist to the effort.
Nevertheless, it was abundantly clear that the hosts were in the mood from an attacking perspective, particularly through the irrepressible Lawson who collected a loose ball from a free-kick and shot over from the edge of the penalty area.
Burnside was then released by Adamson, his Alloa Athletic teammate, but the Northern Irishman’s left-footed strike deflected into the side netting just as space opened up.
And it was no surprise that the equaliser arrived down the right-hand side.
Lawson was at the heart of it as he tempted Kerr in-behind from full-back and his cross-cum-shot from a tight angle looped delightfully over Brian Kinnear and into the far corner.
Clyde had already been forced into a double change by the 38th minute when Robbie Leitch and Thomas Robson limped off, and they were forced into a third substitute before the interval when captain and goalscorer Dunnihy was unable to continue.
It hardly curbed the visitors’ endeavour, however, as Halliwell was forced into a terrific stop at full-stretch when Cannon unleashed at goal in search of his second of the first-half.
Half-time prompted the introduction of Lewis Stewart for the hosts, who has enjoyed an excellent campaign himself at Alloa in their chase for promotion.
It was another Wasps loanee who threatened just minutes into the second period when James Reid strode out of defence and thread a gorgeous pass through the heart of the Clyde rearguard. Burnside couldn’t quite sort out his feet to dig out a shot at goal.
Like Lawson down the opposite end, the away side’s most likely route to goal appeared through the dangerous Cannon, who done well to dart to the near post and meet a low cross which a combination of Halliwell and Reid managed to scramble clear for Rangers.
There was nothing the Gers goalkeeper could do moments later when Clyde took the lead for the third time on the evening. A free-kick right-of-centre 25 yards out was curled around the wall by Connell and in off the inside of the near post.
And yet the home side’s persistence could not be questioned as the riposte arrived less than a minute later.
It was silky footwork from Adamson which engineered the move, dancing across the byline and through several Clyde challenges before laying the ball on a plate across the six-yard box for Stewart to tap home from point-blank range.
Suddenly it was all to play for in a contest which continued to swing one way and another.
Neat interplay involving Aiden Crilly and substitute Kyle Glasgow almost engineered a fourth for the home side, but the former’s low strike was saved smartly by Kinnear at his near post.
The game ticked into its final 20 minutes – with a penalty shootout in store in the event of a draw – as a straight ball through the middle of the Gers rearguard released Cannon through with only Halliwell to beat, but the goalkeeper was alert to deny the attacker at his near post.
From a resulting long throw-in by Connell, the ball sailed into the six-yard area where Scott Williamson reacted first to finish beyond Halliwell and edge Clyde ahead once again.
Opportunity beckoned for Stewart with five minutes remaining to level when he swept goalwards from a Glasgow lay-off, but his strike trickled wide of the far post.
It proved one of the final acts of the contest as the young side couldn’t quite muster a leveller for the fourth time in the game to keep their campaign alive.
RANGERS: Halliwell, Kerr, Wyllie, J. Reid, Wark (Hutton, 80), McCallion, Crilly (Fernie, 80), Adamson, Lawson, Burnside (Glasgow, 58), Cameron (Stewart, 45)
Subs not used: S. Reid (GK), Owen, Young, Rankin
CLYDE: Kinnear, Lyon, Robson (Hynes, 38), Cuddihy (Murdoch, 43), Leitch (Redfern, 38), Dunachie (Williamson, 45), Connell (Scullion, 72), Niang, Fleming, Connolly, Cannon
Subs not used: Hogarth (GK)
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