Conor O’Shea was left shaking his head after missing out on a farewell trophy as French side Montpellier beat his Harlequins side in the Challenge Cup final in Lyon.
With time expired and Harlequins trailing by seven points, substitute Ben Botica had possession of the ball in his own half.
He decided to kick for terrirotory though, gifting the ball to Montpellier who ran it out and, with it, ran out winners in a punishing final.
A converted try from Jesse Mogg gave the French side the lead but the boot of Nick Evans kept Harlequins within four points at the break, trailing 13-9.
Mogg added a second try early in the second half though, meaning Marland Yarde’s score in the final ten minutes was in vain and Harlqeuins missed out on a record fourth Challenge Cup.
Montpellier conceded the first penalty in the fourth minute as Bismarck du Plessis infringed at the breakdown, Evans then did the honours with the boot to put Harlequins 3-0 up.
The French side were back on level terms four minutes later though as Demetri Catrakilis converted from close to the touchline as Harlequins were penalised at the scrum.
The penalties kept coming but Evans failed to give Harlequins another lead in the 12th minute after Timoci Negusa was penalised, the fly-half bouncing his kick off the upright.
As the clock approached 20 minutes the Montpellier pack began to dominate and a rolling maul got them into the Harlequins 22, but the English side turned it over and Danny Care nearly ran the length of the field after hacking clear, but Benjamin Fall smothered the loose ball before the scrum-half could reach it.
Montpellier did break through in the 22nd minute though as Frans Steyn threw a long pass to the left flank, which eventually found its way to substitute Mogg who finished in the corner, Catrakilis adding the extras.
The South African then extended Montpellier’s lead to ten just before the half hour, from the kicking tee, but Evans returned the favour minutes later to bring Harlequins within seven again.
And Evans further reduced the lead with a little over five first-half minutes to go as Montpellier continued to give away penalties and the sides went in at half-time separated by just four points.
On each of the three occasions Harlequins previously won the Challenge Cup they had come from behind at half-time and they had another chance to chip away at Montpellier’s lead in the 44th minute, but Evans missed a relatively straight forward shot at the posts.
Montpellier’s bulk in the pack continued to show it's worth after 45 minutes but Catrakilis stumbled with the try line at his mercy after a dominant rolling maul put the French side within touching distance.
Moments later their advantage did pay though, the fly-half chipping a diagonal kick into the in-goal area for Mogg to leap above Jamie Roberts and ground the ball before he lost control – Catrakilis adding the extras.
With more than 25 minutes to go Evans refused a kick at the posts, opting for a kick to the corner and a possible drive for the line but Sam Twomey fumbled the lineout and the advantage was lost.
Catrakilis then made the Aviva Premiership Rugby side pay in the 55th minute, kicking a penalty to give Montpellier a 14-point lead.
Harlequins came to life with 20 minutes to go but Yarde was brought down just shy of the line, after an initial break from George Lowe, and in the resultant phase Tim Visser dropped Mike Brown’s cross-field kick when in sight of the line.
The inability to convert chances continued to cost Harlequins as, with 13 minutes remaining, Catrakilis put Montpellier 17 points ahead after the English side brought Fulgence Ouedrogo down at a lineout.
With eight minutes to go though Harlequins did score a try, Chris Robshaw’s break finished off by Yarde with the substitute fly-half, Montpellier-bound Botica, converting to reduce the deficit to ten.
Botica then cut the lead to a converted try with three minutes remaining as the Montpellier defence infringed when Harlequins piled on the pressure.
Harlequins thought their game was up when they lost possession in the Montpellier half in the 80th minute but they regained the ball from the French side’s kick and, with the 80 minutes up, they had one last chance to win the game.
However, with time expired, Botica inexplicably kicked for territory when they needed to run the ball and Mogg collected in his own half to run it out and confirm Jake White’s side as the European Challenge Cup winners.
O'Shea now leaves Harlequins, to take over the Italian national side, having won one Challenge Cup, one Premiership Rugby title, and one Anglo-Welsh cup trophy in his six years in charge.
Harlequins: Brown, Yarde, Lowe, Roberts, Visser, Evans (Botica), Care, Marler, Gray (Ward), Jones (Sinckler), Horwill, Twomey, Robshaw, Wallace (Clifford), Easter
Replacements: Lambert, Luamanu, Dickson, Chisholm
Montpellier: Fall (Mogg), Nagusa, Tuitavake (Ebersohn), Steyn, O'Connor, Catrakilis, White (Paillaugue), Nariashvili (Watremez), B Du Plessis (Ivaldi), Jannie Du Plessis (Kubriashvili), Jacques Du Plessis (Timani), Willemse, Ouedraogo, Qera, Spies (Galletier)
Penalties: Evans 3, Botica
Tries: Mogg 3
Conversions: Catrakilis 2
Penalties: Catrakilis 4
Referee: John Lacey
If you want to be at the world's biggest club rugby final, this year's Aviva Premiership Rugby Final is on 28 May at Twickenham, tickets are available from premiershiprugby.com/final