Neil McCallum chipped in with 54, while Kyle Coetzer made 35 before he was run out.
Veteran 19th seed Amanda Coetzer also needed three sets to see off Yugoslavia's Jelena Jankovic 6-2 4-6 6-4.
Italy's Silvia Farina Elia edged South Arican Amanda Coetzer 7-6 7-6 to reach the second round in Filderstadt.
Durham batsman Coetzer smashed his 127 off 141 balls after being put into bat in their third Group A match.
Back came Butler, who had Coetzer caught behind before clean-bowling Colin Smith.
Gordon Drummond skippers the side, while Kyle Coetzer, Fraser Watts and Gregor Maiden are the only survivors from the successful 2004 squad.
Flintoff had Kyle Coetzer fending a short ball to Loye in the slips, bowled Ben Harmison, had Steve caught behind and bowled Claydon.
But Coetzer prodded the next ball tamely to Warne at short extra-cover and Chanderpaul was run out when Collingwood rejected a second run.
Kyle Coetzer's excellent knock of 127 and a four-wicket haul from Jan Stander saw the Scots secure their second group win in three games.
The other upset of the day came in the women's draw, as third seed Jelena Dokic went down 7-6 3-6 6-3 to Amanda Coetzer.
Neil McCallum and Ross Lyons join Hamilton, Watson and Coetzer as the only players remaining from the side that faced England two years ago.
Gavin Hamilton (12) also succumbed early in Scotland's innings, but Coetzer found an able partner in Navdeep Poonia (79) as the pair found their rhythm.
He struck first by having Kyle Coetzer caught at first slip for six and won an lbw verdict against Qasim Sheikh with his next delivery.
Even after Watson finally fell to Ian Butler, holing out in the covers, Kyle Coetzer smashed his first ball for four and the onslaught continued apace.
From the horrors of 13-4, Coetzer established something of a foothold for the Scots, but soon lost partners Neil McCallum and Jan Stander to Johan Botha's accurate off-breaks.
First the Canada seamer had Gavin Hamilton, playing a poor shot, caught behind by Bagai for seven, followed by Kyle Coetzer, who also edged behind to the wicketkeeper.
Flintoff put Lancashire in an even stronger position late in the day when removing Mark Stoneman, Kyle Coetzer and England colleague Paul Collingwood, all caught behind by wicket-keeper Luke Sutton.
Sangakkara played elegantly before he slashed a wide ball from Liam Plunkett to point, where Kyle Coetzer parried the ball above his head and caught it at the fourth attempt.
BBC: SPORT | Cricket | Counties | Chanderpaul fails on home debut
It became an exercise in damage limitation for the remaining Scottish batting, but the talented Coetzer, a Durham pro, was good enough to hit Morkel for a couple of sixes.
In an otherwise untidy Scottish display in the field, Kyle Coetzer's stunning one-handed effort at long-on in the final over to remove Mark Boucher was an early contender for catch of the tournament.
The gentle medium pace of Jesse Ryder, who was called on to bowl the fifth over, could not staunch the flow: Coetzer drilled a wonderful six over wide mid-off either side of two further boundaries.
World number 131 Scheepers had beaten Gisela Dulko, a player ranked 86 places above her, previously in her campaign as she became the first South African to reach the last 16 since Amanda Coetzer in 1997.
Kyle Coetzer needed four more deliveries to reach his half century and when he thrashed Ervine, a match-winner at Lord's in the 2005 final, into the top tier of the grandstand, it looked grim for Hampshire.
On top of half centuries from Shivnarine Chanderpaul (54) and Phil Mustard (50), Kyle Coetzer gave them a big finish as he hit three fours in an over off Chris Tremlett in plundering 29 not out off 18 balls.
Hamilton, who made 48 but announced after the game that he was set to retire from international cricket, added 86 with Coetzer (51) for the second wicket after Ryan Watson fell in the first over, although the Scots were eventually dismissed for 211.
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