if I'm not mistaken, there have been 19 successful MITB cash-ins. so, here's my ranking of each one + personal thoughts on each one.

19. Brock Lesnar cashes in on Seth Rollins [Extreme Rules 2019]

thoughts: he shouldn't have even won the briefcase, let alone cash in successfully.

18. Jack Swagger cashes in on Chris Jericho [Smackdown: April 2, 2010]

thoughts: don't care.

17. Rob Van Dam wins his pre-announced cash-in match against John Cena [One Night Stand 2006]

thoughts: never cared about RVD, nor did I care about this title win.

16. Kane cashes in on Rey Mysterio [Money in the Bank 2010]

thoughts: rey mysterio robbed yet again.

15. Alberto Del Rio cashes in on CM Punk [Summerslam 2011]

thoughts: i might have ranked this higher, had the cash-in not come at the expense of punk

14. Daniel Bryan cashes in on Big Show [TLC 2011]

thoughts: from now on are all the cash-ins that i loved. this one was so out of the blue tbh but it was great. michael cole sold this wonderfully lmao

13. Edge cashes in on The Undertaker [Smackdown: May 8th, 2007]

thoughts: loved it, dunno what else to say tbh.

12. Edge cashes in on John Cena [New Year's Revolution 2006]

thoughts: very first cash-in so i put it above his second cash-in. i pretty much share the same thoughts tho.

11. Bayley cashes in on Charlotte [Money in the Bank 2019]

thoughts: never was a fan of bayley (until her current heel run which i really love), but i couldn't help but smile and feel happy for her.

10. Alexa Bliss cashes in on Nia Jax [Money in the Bank 2018]

thoughts: we all knew she was just a transitional champ for Ronda but still, PRETTY ICONIC i'd say

9. CM Punk cashes in on Jeff Hardy [Extreme Rules 2009]

thoughts: absolutely amazing, and the fact jeff actually kicked out of the gts made this even more iconic

8. Sheamus cashes in on Roman Reigns [Survivor Series 2015]

thoughts: i really don't know why i like this so much, but i just do.

7. Randy Orton cashes in on Daniel Bryan [Summerslam 2013]

thoughts: truly one of the most iconic cash-ins.

6. CM Punk cashes in on Edge [RAW: June 30th, 2008]

thoughts: i always get chills WHAT A MOMENT!!!!

5. Carmella cashes in on Charlotte [Smackdown: April 10th, 2018]

thoughts: the kick didn't connect, but this was a great cash-in to cap off an entertaining run with the briefcase!

4. The Miz cashes in on Randy Orton [RAW: November 22, 2010]

thoughts: IMO the most underrated cash-in. one of my favs certainly

3. Dean Ambrose cashes in on Seth Rollins [Money in the Bank 2016]

thoughts: do I even need to say anything about this iconic night?

2. Seth Rollins cashes in on Brock Lesnar & Roman Reigns [WrestleMania 31]

thoughts: the video speaks for itself.

1. Dolph Ziggler cashes in on Alberto del Cunt [RAW: April 8th, 2013]

thoughts: sad his reign was cut short but the pop he got and the victory was....whew.