Chesswood Group Limited is the subject of an active proceeding under the Companies' Creditors Arrangement Act in the Ontario Superior Court of Justice (Commercial List), court file CV-24-00730212-00CL. As at October 24, 2024, according to a draft Statement of Claim, Chesswood Group Ltd. owed the syndicated lenders under the Syndicated Revolving Credit Facility C$92,797,926.72 and, separately, US$66,254,723.30; the two components are in different currencies and cannot be added, and both exclude unquantified costs, expenses, interest and letter-of-credit amounts. The facility arises under a credit agreement dated January 14, 2022 with an original maximum principal amount of US$300 million. The lending syndicate comprises Royal Bank of Canada, The Toronto-Dominion Bank, The Huntington National Bank, M&T Bank, Canadian Imperial Bank of Commerce and Laurentian Bank of Canada.
The officer filed a report. The CCAA proceedings are substantially complete and awaiting service of the termination certificate. The Debtors are bankrupt and administered on a consolidated basis; the report deals with a class action plaintiff's motion to lift the BIA stay, on which the Trustee takes no position.
Motion Record of the Class Action Plaintiff (Lifting the Stay of Proceedings) — Application / notice of application
Motion Record of the Class Action Plaintiff (Lift Stay Order) — Application / notice of application
Endorsement of Justice FL Myers (Daniel Wittlin - Motion to Strike)* — Application / notice of application
Amended Statement of Claim (Royal bank of Canada v. Chesswood Group Ltd. et al.) — Application / notice of application
Motion Record of Royal Bank of Canada, in its capacity as administrative and collateral agent (Lift Stay Order) — Application / notice of application
Endorsement of Justice Cavanagh (Stay Extension and Ancillary Relief Order) — Endorsement / reasons
The officer filed report no. Supplement to the Eighth Report. The CCAA Parties' businesses have been sold and there are no remaining business activities; only wind-down activities remain (tax filings, records retention). The Monitor seeks a stay extension to January 30, 2026, authority for Canadian CCAA Parties to make bankruptcy assignments, and further distributions to the Pre-Filing Lenders, who face a significant shortfall.
Supplementary Motion Record of the Monitor (Stay Extension and Ancillary Relief) — Application / notice of application
The court granted an approval and vesting order for the sale to 17208260 Canada Inc. Closing terms, as extracted: vesting effective upon delivery of the Monitor's Certificate confirming payment of cash proceeds and satisfaction/waiver of closing conditions.
Motion Record of the Monitor (Easy Legal AVO and CCAA Termination Order) — Application / notice of application
The court granted an approval and vesting order for the sale to North Mill Equipment Finance, LLC. Closing terms, as extracted: Vesting occurs upon delivery of Monitor's Certificate confirming satisfaction/waiver of closing conditions.
The court granted an approval and vesting order for the sale to Axis Holdings Ltd. Closing terms, as extracted: vesting effective upon delivery of Monitor's Certificate confirming satisfaction/waiver of closing conditions.
Endorsement of Justice Kimmel (Waypoint AVO and Fourth Stay Extension Order) — Endorsement / reasons
Factum of the Monitor (Approval and Vesting Order and Fourth Stay Extension) — Approval and vesting order
Motion Record of the Monitor (Approval and Vesting Order and Fourth Stay Extension Order) — Approval and vesting order
Endorsement of Justice Dietrich (Stay Extension and Ancillary Relief Order) — Endorsement / reasons
Motion Record of the Monitor (Third Stay Extension Order and Ancillary Relief) — Application / notice of application
Endorsement of Justice Osborne (Approval and Reverse Vesting Order and Stay Extension Order) — Endorsement / reasons
Motion Record of the Monitor (Approval and Reverse Vesting Order and Stay Extension Order) — Application / notice of application
The court granted an approval and vesting order for the sale to Vault Auto Finance Corporation. Closing terms, as extracted: Vesting occurs upon delivery of the Monitor's Certificate confirming payment of the Purchase Price and satisfaction/waiver of closing conditions.
Source: Approval and Vesting Order
The court granted an approval and vesting order for the sale to Vault. Closing terms, as extracted: closing condition regarding consent and waiver of certain rights with Securitization Parties.
Source: Endorsement of Justice Osborne (Approval and Vesting Order and Stay Extension Order)
Factum of the Monitor (Approval and Vesting Order and Stay Extension Order) — Approval and vesting order
Motion Record of the Monitor (Approval and Vesting Order and Stay Extension Order) — Approval and vesting order
The court approved a sale and investment solicitation process. A bid deadline of 2025-01-20.
Source: SISP Approval Order
Case update
Chesswood: the investor class action comes back for the bankruptcy stay
Cleared by the CCAA court on July 16, the proposed securities class action against Chesswood Group and its former chief executive and chief financial officer now asks the bankruptcy court, in a motion returnable October 1, to lift the s. 69.3 BIA stay as well, pleading that any recovery is limited to Chesswood's insurance; the bankrupt lists no asset of realizable value against $84,222,005.13 in claims.
Debtor
Chesswood Group Limited
Monitor
FTI
Bench
| Judge | Court | On this docket | Cases on record |
|---|---|---|---|
| Justice Kimmel | Ontario Superior Court of Justice | 12 orders, Oct 2024 – Sep 2025 | 198 cases on record |
| Justice Cavanagh | Ontario Superior Court of Justice | 6 orders, Oct 2025 – Jan 2026 | 318 cases on record |
| Justice Osborne | Ontario Superior Court of Justice | 5 orders, Jan 2025 – Mar 2025 | 168 cases on record |
| Justice Dietrich | Ontario Superior Court of Justice | 2 orders, May 2025 – Jul 2026 | 132 cases on record |
Counsel of record
| # | Priority class | Creditor | Amount | Source |
|---|---|---|---|---|
| 4 | Secured | Royal Bank of Canada, as Administrative Agent and Collateral Agent, and the Existing Lenders (The Toronto-Dominion Bank, The Huntington National Bank, M&T Bank, Canadian Imperial Bank of Commerce, LauGeneral security agreement dated December 8, 2014 (Borrower) and individual security agreements (Guarantors) over all present and after-acquired property, pursuant to second amended and restated credit agreement dated January 14, 2022 (Existing Credit Agreement) — CAD portion of total outstanding under Credit Facilities; plus costs, expenses and accruing interest; excludes outstanding letters of credit (reported separately) — debtor: Chesswood Group Limited and Existing Guarantors (Case Funding Inc., Chesswood Holdings Ltd., Chesswood US Acquisitionco Ltd., Pawnee Leasing Corporation, Lease-Wi · as of 24 Oct 2024 | $92.8M | Notice of Application of Royal Bank of Canada |
| 4 | Secured | |||
| 4 | Secured | |||
| 4 | Secured | |||
| 8 | Unsecured | |||
| 8 | Unsecured | |||
| 8 | Unsecured | |||
| 8 | Unsecured | |||
| 8 | Unsecured | |||
| 8 | Unsecured |
34 more claims in 2 classes The stack holds Secured and Unsecured claims.
Every creditor and every amount, drawn to scale.
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See all plans11 transactions · 9 closed · 2 approved — the Monitor has successfully completed the SISP and has identified and implemented five separate value maximizing transactions resulting in realization in excess of $130 millionNinth Report of the Monitor · 18 Jan 2026
| Purchaser | Price | Status | Source |
|---|---|---|---|
| Vaultall assets owned by the Vendors (excluding Excluded Assets) · asset sale · nominee/assignee: an affiliate · agreement 23 Jan 2025 | Subscribers | Approved29 Jan 2025 | Endorsement of Justice Osborne (Approval and… |
| Vault Auto Finance Corporationall of the applicable Vendors' right, title and interest in and to the Purchased Assets · asset sale · nominee/assignee: a permitted assignee thereof · agreement 23 Jan 2025 | Subscribers | Closed14 Feb 2025 | Ninth Report of the Monitor |
| North Mill Equipment Finance, LLCthe Purchased Shares · share sale · ResidualCo: CGL Holdco, LLC · agreement 28 Feb 2025 | Subscribers | Closed1 Apr 2025 | Ninth Report of the Monitor |
| Axis Holdings Ltd.all of the Vendor's right, title and interest in and to the Purchased Shares · share sale · agreement 6 Jun 2025 | not stated | Approved9 Jun 2025 | Waypoint Approval and Vesting Order |
| North Mill Equipment Finance, LLCall of the issued and outstanding shares in the capital of Pawnee and Tandem · share sale · agreement 28 Feb 2025 | not stated | Closed | Seventh Report of the Monitor |
| Vault Auto Finance Corporation100% of the issued and outstanding shares of Rifco Inc. · asset sale · agreement 13 Dec 2024 | Subscribers | Closed | Seventh Report of the Monitor |
| North Mill Equipment Finance, LLCall of the Vendor's right, title and interest in and to the Bishop Equity Interests and the Bishop Assigned Contract · assets and shares · agreement 22 Jul 2025 | Subscribers | Closed18 Aug 2025outside 29 Aug 2025 | Ninth Report of the Monitor |
| 17208260 Canada Inc.all of the applicable Vendors' right, title and interest in and to the Purchased Assets · asset sale · agreement 27 Aug 2025 | Subscribers | Closed23 Sep 2025 | Ninth Report of the Monitor |
| unnamedthe Transactions | not stated | Closed23 Sep 2025 | Monitor's Certificate |
| shares of Waypoint sold by CCMI; purchaser not namedall issued and outstanding shares of Waypoint Investment Partners Inc. · share sale · agreement 6 Jun 2025 | not stated | Closed | Ninth Report of the Monitor |
| unnamedthe Waypoint Transaction | not stated | Closed15 Aug 2025 | Ninth Report of the Monitor |
Unsecured creditors: no distribution. Pre-Filing Lenders short.EstimatedReport of the Trustee (BIA Lift Stay Motion) · 28 Sep 2026
| Class | Creditor | Claims | Recovery | Basis | Source |
|---|---|---|---|---|---|
| Secured | Chesswood Group's pre-filing secured creditors | — | shortfall | Estimatedper the monitor | Supplement to the Fifth Report of the Monitor · 30 Apr 2025 |
| Secured | Pre-Filing Agent / Pre-Filing Lenders | — | shortfall | Estimatedper the monitor | Ninth Report of the Monitor · 18 Jan 2026 |
| Secured | Pre-Filing Lenders | — | shortfall | per the monitor | Motion Record of the Monitor (CCAA Termination Order) · 18 Jan 2026 |
| Unsecured | creditors in the bankruptcy | — | no distribution | Estimatedper the trustee | Report of the Trustee (BIA Lift Stay Motion) · 28 Sep 2026 |
Each row is one filing's statement, copied as it reads and never computed. "Estimated" is the officer's forecast; "Under the plan" is the plan's or proposal's own term; "Final" is a declared or paid distribution; a row with no chip states no footing. A range is the two numbers stated; "of proven claims" is the document's own denominator.
7 engagements · 2 firms — latest: Osler, Hoskin & Harcourt LLP, 1 Sep 2025 – 12 Jan 2026Ninth Report of the Monitor · 18 Jan 2026
| Firm | Period | Hours | Fees | Rates | Source | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| FTI Consulting Canada Inc.Monitorperiod 3 of 3 | 1 Sep – 31 Dec 2025Sought | — | Ninth Report of the Monitor · 18 Jan 2026 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| FTI Consulting Canada Inc.Monitorperiod 2 of 3 | 1 Aug – 31 Aug 2025 | 7 people | Supplementary Motion Record of the Monitor (Stay Extension and… · 26 Sep 2025 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
7 people — FTI Consulting Canada Inc., 1 Aug – 31 Aug 2025 · 23 blurred figures
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| FTI Consulting Canada Inc.Monitorperiod 1 of 3 | — | — | Fifth Report of the Monitor · 25 Apr 2025 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Osler, Hoskin & Harcourt LLPCounsel to the monitorperiod 4 of 4 | 1 Sep 2025 – 12 Jan 2026Approved | — | Ninth Report of the Monitor · 18 Jan 2026 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Osler, Hoskin & Harcourt LLPCounsel to the monitorperiod 3 of 4 | 12 Feb – 31 Aug 2025 | — | not stated | Supplementary Motion Record of the Monitor (Stay Extension and… · 26 Sep 2025 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Osler, Hoskin & Harcourt LLPCounsel to the monitorperiod 3 of 4 | 1 Aug – 31 Aug 2025 | 12 people | Supplementary Motion Record of the Monitor (Stay Extension and… · 26 Sep 2025 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
12 people — Osler, Hoskin & Harcourt LLP, 1 Aug – 31 Aug 2025 · 24 blurred figures
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Osler, Hoskin & Harcourt LLPCounsel to the monitorperiod 1 of 4 | 29 Oct 2024 – 28 Feb 2025 | — | Fifth Report of the Monitor · 25 Apr 2025 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
62 blurred figures above
What each firm billed, and each person’s hours and rate — each as the filing states it, with its source.
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See all plansAs at ·
Professional fees
$282K
As at 31 Aug 2025Supplement to the Eighth Report of the Monitor
The total the debtor stated at filing
Each one as the filing states it, with its source.
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See all plans| Date | Document | File |
|---|---|---|
Report of the Trustee (BIA Lift Stay Motion)
| PDF · Subscribers | |
| Motion Record of the Class Action Plaintiff (Lifting the Stay of Proceedings) | PDF · Subscribers | |
Service List
| PDF · Subscribers | |
Lift Stay Order (Class Action Plaintiff)
| PDF · Subscribers | |
Motion Record of the Class Action Plaintiff (Lift Stay Order)
| PDF · Subscribers | |
Endorsement of Justice FL Myers (Daniel Wittlin - Motion to Strike)*
| PDF · Subscribers | |
| Form 19 - Certificate of Appointment | PDF · Subscribers | |
| Form 78 - Statement of Affairs | PDF · Subscribers | |
CCAA Termination Order
| PDF · Subscribers | |
Endorsement of Justice Cavanagh (CCAA Termination Order)
| PDF · Subscribers | |
Motion Record of the Monitor (CCAA Termination Order)
| PDF · Subscribers | |
Ninth Report of the Monitor
| PDF · Subscribers | |
| Amended Statement of Claim (Royal bank of Canada v. Chesswood Group Ltd. et al.) | PDF · Subscribers | |
Aide Memoire of Daniel Wittlin
| PDF · Subscribers | |
Endorsement of Justice Cavanagh (Lift Stay Order)
| PDF · Subscribers | |
Lift Stay Order
| PDF · Subscribers | |
Factum of Royal Bank of Canada, in its capacity as administrative and collateral agent (Lift Stay Order)
| PDF · Subscribers | |
| Notice of Appearance - Daniel Wittlin | PDF · Subscribers | |
Blackline to the Revised Draft Order of Royal Bank of Canada, in its capacity as administrative and collateral agent (Lift Stay Order)
| PDF · Subscribers | |
Revised Draft Order of Royal Bank of Canada, in its capacity as administrative and collateral agent (Lift Stay Order)
| PDF · Subscribers | |
| Motion Record of Royal Bank of Canada, in its capacity as administrative and collateral agent (Lift Stay Order) | PDF · Subscribers | |
Endorsement of Justice Cavanagh (Stay Extension and Ancillary Relief Order)
| PDF · Subscribers | |
Stay Extension and Ancillary Relief Order
| PDF · Subscribers | |
Supplement to the Eighth Report of the Monitor
| PDF · Subscribers | |
Supplementary Motion Record of the Monitor (Stay Extension and Ancillary Relief)
| PDF · Subscribers | |
Monitor's Certificate
| PDF · Subscribers | |
Easy Legal Approval and Vesting Order
| PDF · Subscribers | |
Endorsement of Justice Kimmel (Easy Legal AVO)
| PDF · Subscribers | |
Factum of the Monitor (Easy Legal AVO and CCAA Termination Order)
| PDF · Subscribers | |
| Eighth Report of the Monitor | PDF · Subscribers | |
| Motion Record of the Monitor (Easy Legal AVO and CCAA Termination Order) | PDF · Subscribers | |
Bishop Approval and Vesting Order
| PDF · Subscribers | |
Endorsement of Justice Kimmel (Bishop AVO)
| PDF · Subscribers | |
| Factum of the Monitor (Bishop Approval and Vesting Order) | PDF · Subscribers | |
| Motion Record of the Monitor (Bishop AVO) | PDF · Subscribers | |
Seventh Report of the Monitor
| PDF · Subscribers | |
Endorsement of Justice Kimmel (Waypoint AVO and Fourth Stay Extension Order)
| PDF · Subscribers | |
Fourth Stay Extension Order
| PDF · Subscribers | |
Waypoint Approval and Vesting Order
| PDF · Subscribers | |
| Factum of the Monitor (Approval and Vesting Order and Fourth Stay Extension) | PDF · Subscribers | |
| Motion Record of the Monitor (Approval and Vesting Order and Fourth Stay Extension Order) | PDF · Subscribers | |
Sixth Report of the Monitor
| PDF · Subscribers | |
Endorsement of Justice Dietrich (Stay Extension and Ancillary Relief Order)
| PDF · Subscribers | |
Factum of the Monitor (Third Stay Extension and Ancillary Relief)
| PDF · Subscribers | |
Supplement to the Fifth Report of the Monitor
| PDF · Subscribers | |
Fifth Report of the Monitor
| PDF · Subscribers | |
| Motion Record of the Monitor (Third Stay Extension Order and Ancillary Relief) | PDF · Subscribers | |
Endorsement of Justice Osborne (Approval and Reverse Vesting Order and Stay Extension Order)
| PDF · Subscribers | |
Approval and Reverse Vesting Order
| PDF · Subscribers | |
Stay Extension Order
| PDF · Subscribers | |
Factum of the Monitor (Approval and Reverse Vesting Order and Stay Extension Order)
| PDF · Subscribers | |
Fourth Report of the Monitor
| PDF · Subscribers | |
Motion Record of the Monitor (Approval and Reverse Vesting Order and Stay Extension Order)
| PDF · Subscribers | |
Approval and Vesting Order
| PDF · Subscribers | |
Endorsement of Justice Osborne (Approval and Vesting Order and Stay Extension Order)
| PDF · Subscribers | |
| Factum of the Monitor (Approval and Vesting Order and Stay Extension Order) | PDF · Subscribers | |
| Motion Record of the Monitor (Approval and Vesting Order and Stay Extension Order) | PDF · Subscribers | |
Third Report of the Monitor
| PDF · Subscribers | |
| Notice of Appearance - Deutsche Bank Trust Company Americas | PDF · Subscribers | |
SISP Notice
| PDF · Subscribers | |
Endorsement of Justice Kimmel
| PDF · Subscribers | |
KERP Approval Order
| PDF · Subscribers | |
SISP Approval Order
| PDF · Subscribers | |
SISP Procedures
| PDF · Subscribers | |
| Motion Record of the Monitor | PDF · Subscribers | |
Second Report of the Monitor
| PDF · Subscribers | |
| Notice of Appearance - VP Polus Trust | PDF · Subscribers | |
Amended and Restated Initial Order
| PDF · Subscribers | |
| Notice of Appearance - Berger Montague | PDF · Subscribers | |
| Notice of Appearance - VersaBank | PDF · Subscribers | |
| Factum of Royal Bank of Canada | PDF · Subscribers | |
| First Report of the Monitor | PDF · Subscribers | |
| Motion Record of Royal Bank of Canada | PDF · Subscribers | |
Application Record of Royal Bank of Canada
| PDF · Subscribers | |
| CCAA FAQs | PDF · Subscribers | |
Initial Order
| PDF · Subscribers | |
| List of Known Creditors | PDF · Subscribers | |
Notice of Application of Royal Bank of Canada
| PDF · Subscribers | |
| Notice to Creditors | PDF · Subscribers | |
Pre-Filing Report of the Proposed Monitor
| PDF · Subscribers | |
Filing titles and dates are public, and so is each filing's own page. The figures read from them are for subscribers.
CiteProceedings., “Chesswood Group Limited” (CCAA), Ontario Superior Court of Justice · Commercial List. Retrieved 5 November 2026, https://proceedings.ca/case/chesswood-group-limited
Sources last checked · summary updated 8 August 2026 · Report a correction · Printed from proceedings.ca/case/chesswood-group-limited
Facts and summaries are extracted automatically from the court filings linked on each page; the filings remain the authoritative record. Suggested corrections are reviewed against the source filings.