Andy Murray has bowed out of the Paris Masters at the first hurdle after losing an all-action contest against Dominik Koepfer.
The three-time Grand Slam winner let seven match points slip through his grasp against Koepfer, who replaced the injured Jenson Brooksby in the tournament.
The final set went down to a nail-biting tie break as Koepfer ultimately prevailed 6-4 5-7 7-6(9) to advance to round two, where he will face Gianluca Mager or Felix Auger-Aliassime.
There was more disappointment for Great Britain as Dan Evans suffered a 6-2 5-7 5-7 defeat to Kazakhstan's Alexander Bublik, but Cameron Norrie eased past Argentina's Federico Delbonis 6-2 6-1.
Murray is due to finalise his 2021 season at the Stockholm Open later this month, although he has refused to rule out a Davis Cup U-turn.