Matthews South

Matthews South

  • About Us
  • Our Solutions
    • Debt
    • Equity
    • IPO
    • Pre-IPO Financing
    • Convertible & Call Spread
      • Call Spread Unwind
      • Liability Management
    • Share Repurchases
      • Accelerated Share Repurchase (ASR)
      • Enhanced Open Market Repurchase (eOMR)
    • Capital Structure Review
  • Our Clients
    • Client List
    • Testimonials
  • Our Team
  • Video Library
  • Blog
  • Contact Us
  • Login

by | August 22, 2026 |

Our Clients

August 10, 2026
$2.175bn + $325mm Greenshoe
Maturity: 5 Years
Execution Structure: 1-Day Public Marketing
Structure: Provisional Call with Make-Whole in Year 3
Coupon: 0.00% (0.00% fixed)
Premium: 60.0% (57.5 - 62.5% marketing range)
Capped Call Upper Strike Price: Up 175.0%
Matthews South Role: Financial Advisor
Lead Left Bookrunner: Goldman Sachs
Active Bookrunners: Citi / Morgan Stanley / Wells Fargo

$2.5 billion Convertible + Capped Call

Transaction and Process Overview


  • Structuring
    • Matthews South advised Cloudflare on its $2.175 billion convertible issuance, representing the company’s fourth equity-linked financing since its 2019 IPO
    • We helped Cloudflare navigate multiple workstreams, focusing on optimal structuring, syndicate selection, documentation, accounting analysis and tax considerations, and pricing and execution of the transaction

  • Capped Call Process
    • Matthews South ran a capped call auction with 20+ banks which were asked to provide pricing on multiple structures and allocations, ultimately allowing Cloudflare to secure efficient pricing with an effective conversion premium of up 175.0%
    • Cloudflare is the only convertible issuer to achieve an upper strike of 175.0% (highest in the corporate call spread market)

  • Marketing and Pricing
    • The offering priced at a 0.00% coupon and 60.0% conversion premium, ranking among the best-priced convertible offerings of the last five years
    • Cloudflare achieved these terms with its stock up 3.5% during marketing, versus declines for similarly priced offerings, making it the strongest overall execution of the period
    • Through efficient pricing on the capped call, the company achieved a 2.2% financing rate with no dilution until a 175% premium

Additional Deals for Cloudflare

  • June 2025: $2bn Convertible + Capped Call
  • August 2021: $1.294bn Convertible + Capped Call
  • May 2020: $500mm Convertible + Capped Call

Contact Us

To learn more about our solutions or to schedule a demo of our software, please contact us by filling out the form below, or email us at info@matthewssouth.com.






    • Matthews South LLC is a member of FINRA and SIPC
    • Brokercheck
    • © Matthews South, Inc. 2025
    • Privacy Policy
    • Additional Disclosure
    • Testimonials may not be representative of the experience of other customers and are not a guarantee of future performance or success