Premiership side St Mirren are out of the Premier Sports Cup – however League Two Annan have reached the knockout stages in dramatic style.
The fourth tier club required just a point from their home match against Ayr United but found themselves a goal down with 20 minutes remaining.
However, Tony Wallace equalised from the spot five minutes into stoppage-time after Dominic Docherty had been sent off before clinching a bonus point in the post-match shootout to book their place in the last 16.
That result means St Johnstone, who won the trophy in 2021 and were semi-finalists last season, are at risk of elimination despite their 4-2 win over Elgin.
Goals from Adam Montgomery, Melker Hallberg, Stevie May and Cammy Ballantyne had them in a comfortable four-goal lead, only for the hosts to pull back two goals late on.
Saints must now better Queen of the South’s result this weekend to stand any chance of progressing as one of the three best group runners up.
Meanwhile, St Mirren are out of the competition after succumbing to a 2-0 defeat at Airdrie.
The 2013 winners were reduced to ten men in the first half following Greg Kiltie’s red card, before goals from Justin Devenny and Kyan Gunn gave the Diamonds all three points.
They will progress automatically as group winners if they beat current leaders Arbroath in 90 minutes on Saturday.
Elsewhere, Aberdeen were 5-0 up at half-time against Stirling Albion to continue their flawless start as goals from Christian Ramirez, Matty Kennedy, Ross McCrorie and a Vicente Besuijen double made it three wins from three for Jim Goodwin’s men.
Raith Rovers won a penalty shoot-out following a goalless clash with Dumbarton to stay in the running for top spot in Group A, but they will need to win by two goals at Pittodrie on Sunday.
Inverness are also unbeaten after a Cameron Harper double and strikes from Billy McKay and Wallace Duffy put them ahead of Premiership Livingston in Group G with a comfortable win over Albion Rovers.
Ross County moved into top spot above Dunfermline in Group C thanks to a 2-0 win at Alloa courtesy of goals from Josh Sims and Jordy Hiwula in a game that also saw The Wasps miss a penalty.
Partick Thistle went back above Kilmarnock to lead Group B. An own goal and a Brian Graham effort earned the Jags a 2-0 home win over Fraserburgh, while Stenhousemuir kept their slim hopes alive with a 2-0 victory at Montrose.
Dundee moved into pole position in Group H when they beat Queen’s Park 2-1. First-half goals from Alex Jakubiak and Cammy Kerr put the visitors in the driving seat at Ochilview and they held on after Louis Longridge pulled a goal back in the 52nd minute.
Hibernian face Greenock Morton at Easter Road on Wednesday while Bonnyrigg Rose take on Falkirk and FC Edinburgh host Cowdenbeath.