Seeing Cillian Sheridan stretchered off “killed the night” for Dundee as they crashed out of the SPFL Trust Trophy at the semi-final stage.
The Dark Blues were cruising 2-0 up against Raith Rovers for much of the contest thanks to a superb double from Lyall Cameron.
However, late goals from William Akio and Sam Stanton saw Raith stage a remarkable comeback.
That forced extra-time and penalties before the returning Zach Robinson saw his final spot-kick come back off the post to see the Kirkcaldy side into the final.
As tough as the defeat was to take after a string of missed chances, Bowyer says it pales into insignificance after seeing Sheridan suffer a potentially serious injury.
The Republic of Ireland international returned from a ruptured Achilles tendon in September after 11 months out but is facing another extended spell on the sidelines.
“Not good, I’m afraid,” Bowyer said when asked about Sheridan’s injury.
“He knew straight away.
“It’s his other Achilles so not good.
“That really killed the night for us.
“It makes everything else irrelevant.
“For him to have come back from the last one as well as he has done, nobody deserves that luck on a football pitch.
“We will look after him and get him back.”
‘Endless chances’
Sheridan went off in stoppage time with Dundee shocked to be heading into extra-time.
Missed chances have been a theme this season for Bowyer’s side.
And this clash took that to a new level as opportunity after opportunity to finish Raith off was passed up.
“We should have had it won after 45 minutes,” the Dundee boss said.
“I thought we played really well bar scoring the goals we should have done.
“Full credit to Raith. We haven’t been able to beat them.
“We said at half-time, don’t think the second half will be the same and we have conceded two poor goals.
“But we still had endless chances to score after that.
“There are lots of positives to take. We got beat and are out of the cup but the way we played and chances created is all positive.
“We should have been out of sight.”
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