Artemis MacAulay Cup holders Kinlochshiel fell at the first hurdle in their defence of the trophy when they lost on penalties to Lovat after 120 goalless minutes at Balmacara.
This was by no means the only shock of this first round, since National Division Fort William ousted 2012 winners, Premiership side Glenurquhart, also on penalties following a 2-2 draw at An Aird.
Elsewhere a winner in the penultimate minute of extra time put Oban Celtic through away to their more fancied National Division colleagues Inveraray, while Kingussie went out 2-0 to Premiership bottom club Lochaber.
Other outcomes were more predictable. Newtonmore won 3-1 on Skye while Oban Camanachd brushed Ballachulish aside 4-0, and Glasgow Mid Argyll progressed 5-1 at Aberdour.
Meanwhile, Kyles went two points clear in the Marine Harvest Premiership with a 3-1 home win over Kilmallie.
Although Lovat and Kinloshshiel are both Premiership teams, Shiel's better recent form, combined with home advantage, meant they were widely tipped to progress, but the 3-2 shootout denied the holders.
Arran MacPhee got Fort off to a great start with the opener but Fraser Heath and James Hurwood had Glen ahead by half time. Then, with just 10 minutes left, MacPhee got the equaliser which sent the tie to extra time, before Fort's 2-0 penalties victory.
At the Winterton, Allan McDonald's hat-trick and one from Ruaridh Graham Junior for cup specialists Inveraray was cancelled out by Lee Askew's opener, one from Daniel Madej and the late saving grace of a Neil Carmichael double for Celtic. This took the game into extra time, in which Daniel MacMillan grabbed the winner in the 119th minute for Celtic in their first season as a national league club.
A Shaun Nicholson brace did the trick for Lochaber as Kingussie failed to score for the third time in four home games this season.
An Andrew McCuish double followed by one each from Daniel MacVicar and Daniel Cameron propelled Oban Camanachd through at Mossfield. Calum McLay's first-half double, split by a Brian Slattery goal, plus one in each half from Craig Anderson, put Mid Argyll 5-0 up before David MacKenzie replied for Aberdour.
Ian Robinson struck first for Newtonmore and Glen MacKintosh made it 2-0 after just nine minutes. However, Skye steadied and James Pringle made it 2-1 on the stroke of half-time before Mackintosh's second rounded it off.
A Robbie MacLeod penalty sent Kyles on their way to the 3-1 victory which extended their 100% Premiership record to five games and opened up a two-point gap over Kinlochshiel. Sandy MacKenzie soon got Kyles' second but Duncan Rodger pulled one back for Kilmallie before Roddy MacDonald put the game to bed.
A 3-0 win for Caberfeidh at Beauly allowed them to narrow Skye's National Division lead to a single point.