Playing his first match since a finger injury while playing for Guyana in the Caribbean Premier League, Guptill flashed at a ball down the leg side only for Cachopa to leap to his left and take a superb one-handed catch.
It wasn't the start the hosts were looking for and it didn't get any better nearly two overs later. Bennett was in the wickets again when Henry Nicholls caught a dying edge at third slip from batsman Tim McIntosh for one to leave Auckland reeling at 22-2.
Cachopa launched the first of two sixes that ended up on Sandringham Road. An ensuing car had rolled over the top and had put grease on the ball, leaving umpires Gary Baxter and Barry Frost no choice but to replace the ball and it immediately paid dividends for the visitors.
Raval, who struggled his way to 19 from 56 deliveries, was trapped in front by Matt McEwen. The medium fast bowler had a wicket in his next over when he bowled Auckland captain Gareth Hopkins for four.
At 73-4 after 20 overs, Auckland still had plenty of work to do. That wasn't helped when the confident-looking Cachopa was caught by Logan van Beek from Shanan Stewart's first over for 31 to leave the hosts shivering at 73-5 after 21 overs.
Stewart had his second wicket of the match soon after when McEwen took a good catch to dismiss Donovan Grobbelaar for four to compound Auckland's misery.
Fulton got in on the action when he took the catch at first slip to dimiss Colin de Grandhomme for 16 as Auckland lost their seventh wicket of the session.
Matt Henry then had two wickets in two deliveries when he clean bowled Bates to sit on a hat trick ball, which was kept out by Bartlett.
Enter Quinn, whose innings provided Canterbury with more than a mouthful ahead of the lunch break.