Dundee United beaten by Rapid Vienna on penalties after thriller at Tannadice
Watters grabbed his second with a penalty three minutes before the break but Rapid striker Janis Antiste reduced the deficit in the 63rd minute with United defender Iurie Iovu involved in the ball finding the net.
Half-time substitute Ercan Kara levelled in the 77th minute to take an open game into extra-time and then penalties, where United substitute Amar Fatah hit the post, the only miss as the visitors triumphed 5-4.
There was no lack of effort from Jim Goodwin's men, who will regroup to take on Kilmarnock at Rugby Park in the Premier Sports Cup on Sunday, knowing that they have European experience to draw upon.
It was an exhausting evening which began with both teams flying at each other from kick off.
United's Vicko Sevelj tested Rapid keeper Niklas Hedl with a drive and Watters missed a chance from a Ivan Dolcek cross, heading wide.
For Rapid, Antiste broke through the United defence and his low drive was pushed behind by United keeper Yevhenii Kucherenko for a corner which was comfortably defended before the striker hit the side netting with a speculative shot on the turn.
The game turned in the Taysiders' favour when Watters, who missed the William Hill Premiership defeat by Hearts at the weekend with a bug, was picked out by stand-in captain Will Ferry's cross to the centre of the goals and he steered a header back across Hedl and into the net.
Rapid retaliated and in the 35th minute Bendeguz Bolla forced a save from Kucherenko with an angled-drive, again the corner fizzling out.
United striker Zac Sapsford slalomed through the Rapid defence but his pass to Watters was overhit.
However, Sapsford was wiped out by Rapid centre-back Serge-Philippe Raux-Yao before releasing the ball and, after looking at the pitchside monitor at the behest of his VAR, Greek referee Tasos Sidiropoulos pointed to the spot and Watters sent Hedl the wrong way with his spot kick.
Sapsford was replaced by Fatah for the start of the second half and, after repelling expected Rapid pressure, Ferry volleyed just off target in a United counter before Kecherenko made saves from Petter Dahl and Kara.
Peter Stoger's side kept going and got a lifeline when Antiste glanced in a near-post corner from Bolla and in the 72nd minute Kucherenko was at full stretch to brilliantly save Kara's curling shot from inside the box.
The equaliser looked inevitable, however, and arrived when substitute Nikolaus Wurmbrand crossed and Kara knocked it past Kucherenko from six yards.
The match had turned completely and moved into extra-time where United came back into the game and in the 100th minute Hedl saved a dink from United's Owen Stirton after the United substitute raced on to a slack back header by Nenad Cvetkovic.
The home fans rallied their side but the second half of extra-time could not produce a winner – Kara headed over from a corner with the last action – and so the tie went to penalties, where the home side fell short.
After Fatah hit the post with the first penalty, Ferry, Bert Esselink, Sveljt, Krisztian Keresztes all scored for the home side but so did Kara, Claudy Mbuyi, Andrija Radulovic, Raux-Yao and Bolla for the visitors.
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