Exhibit 10.1

EXECUTION VERSION

John Orr

Kansas City

Dear John:

This letter agreement (this “Agreement”) memorializes the terms we have agreed regarding your resignation of employment with Soo Line Railroad Company, a subsidiary of Canadian Pacific Kansas City Limited (together with its subsidiaries, the “Company”), effective March 19, 2024 (the “Separation Date”).

1. Unpaid Salary, Accrued Vacation, and Expenses

On or prior to the first regular payroll date of the Company following the Separation Date, the Company will pay you a lump sum amount equal to (i) any accrued but unpaid base salary, (ii) any unpaid or unreimbursed business expenses, (iii) any accrued but unused vacation, and (iv) any other amounts owing, but still unpaid, to you up to the Separation Date (the “Accrued Obligations”).

2. Relocation Repayment

The Company hereby waives your obligation to repay a prorated portion of the relocation costs incurred by the Company in connection with your commencement of employment with the Company, as set forth in the terms of Appendix I to the employment letter, dated as of March 23, 2023, between you and the Company.

3. Forfeiture of Equity Awards

Your outstanding, unvested Company equity awards will be forfeited on the Separation Date, in accordance with their terms.

4. Limited Waiver of Non-Competition Provisions

The Company hereby agrees to waive the enforcement of the non-competition provisions set forth in (i) Section 7(b)(i) of the Amended and Restated Severance Agreement, dated as of September 15, 2021, between you and Kansas City Southern Railway Company (the “Severance Agreement”), (ii) Section 3(b) of the Non-Competition and Non-Solicitation Agreements, dated as of April 28, 2023, between you and the Company (the “April 2023 Non-Competition Agreements”), and (iii) Section 3(b) of the Non-Competition and Non-Solicitation Agreement, dated as of May 17, 2023, between you and the Company (together with the April 2023 Non-Competition Agreements, the “Non-Competition Agreements”), and any other non-competition provision relating to the Company to which you would otherwise be subject, each solely with respect to your future employment with Norfolk Southern Corporation (the “Non-Competition Waiver”).

The Non-Competition Waiver is conditioned on and subject to:

5. Non-Solicitation Provisions

You continue to remain subject to the non-solicitation provisions set forth in (i) Section 7(b)(ii) of the Severance Agreement and (ii) Section 3(c) of the Non-Competition Agreements.

Further, you agree that during the two (2) years following the Separation Date, you may not (i) encourage, induce, or solicit any employee of the Company to leave the employ of the Company or (ii) assist any other person to encourage, induce, or solicit any employee of the Company to leave the employ of the Company.

6. Additional Restrictive Covenants

You hereby reaffirm your ongoing obligations under Severance Agreement, the Non-Competition Agreements and any other agreements with the Company, in accordance with their terms, except as explicitly amended herein.

Notwithstanding the confidentiality provisions set forth in (i) Section 7(a) of the Severance Agreement and (ii) Section 4(d) of the Non-Competition Agreements, nothing shall limit your rights under applicable law to initiate communications directly with, provide information to, respond to any inquiries from, or report possible violations of law or regulation to any governmental entity or self-regulatory authority, or to file a charge with or participate in an investigation conducted by any governmental entity or self-regulatory authority, and you do not need the Company’s permission to do so. In addition, it is understood that you are not required to notify the Company of a request for information from any governmental entity or self-regulatory authority or of your decision to file a charge with or participate in an investigation conducted by any governmental entity or self-regulatory authority. Notwithstanding the foregoing, you recognize that, in connection with the provision of information to any governmental entity or self-regulatory authority, you must inform such governmental entity or self-regulatory authority that the information you are providing is confidential. Despite the foregoing, you are not permitted to reveal to any third party, including any governmental entity or self-regulatory authority, information you came to learn during your service to the Company that is protected from disclosure by any applicable privilege, including but not limited to the attorney-client privilege or attorney work product doctrine. The Company does not waive any applicable privileges or the right to continue to protect its privileged attorney-client information, attorney work product, and other privileged information.

7. Return of Confidential Information

You hereby agree that, promptly following the Separation Date, you will deliver to the Company all documents, media and other items in your possession containing confidential information of the Company or any subsidiary, including all complete or partial copies, recordings, abstracts, notes or reproductions of any kind made from or about such documents, media, or items or information contained therein.

8. Governing Law

This Agreement shall be construed according to the laws of the State of Minnesota.

9. Remedies

In addition to any remedies that may be available at law or in equity as a result of a breach of this Agreement, in the event of a breach, deemed breach, or threatened breach by you of any of the provisions herein, the Company shall have the right to seek monetary damages and equitable relief, including, without limitation, specific performance by means of an injunction against you to prevent or restrain any such breach.

10. Amendments and Waivers

No amendments to this Agreement shall be valid or binding unless in writing and duly executed by both parties. No waiver of any breach of any term or provision of this Agreement shall be binding unless made in writing and signed by the party purporting to give the same and, unless otherwise provided in the written waiver, shall be limited to the specific breach waived.

11. Severability

If any provision of this Agreement or its application in a circumstance is restricted, prohibited or unenforceable, the provision shall be ineffective only to the extent of the restriction, prohibition or unenforceability without invalidating the remaining provisions of this Agreement and without affecting its application to other circumstances.

12. Counterparts; Attorneys Fees

This Agreement may be executed in counterparts and delivered by means of facsimile, portable document format (PDF) or electronic signature, each of which when so executed and delivered shall be an original, but all such counterparts together shall constitute one and the same instrument. The Company will pay directly to your counsel the attorney’s fees incurred in connection with the review, legal analysis, drafting and negotiation of this Agreement in the fixed amount of $15,000 promptly following the date of this Agreement.

[SIGNATURE PAGE FOLLOWS]

Please confirm your acceptance of the foregoing by signing below.

I agree with and accept the foregoing terms.

Appendix A

RELEASE

Exhibit 99.1

Release:  March 20, 2024

CPKC announces departure of Executive Vice President and Chief Transformation Officer

Calgary – Today, Canadian Pacific Kansas City (TSX: CP) (NYSE: CP) (CPKC) announced the departure of John Orr, Executive Vice President and Chief Transformation Officer. Mr. Orr will be joining Norfolk Southern as their Chief Operating Officer.

“On behalf of the Board of Directors and the CPKC family I would like to thank John for his contributions and impactful leadership,” said CPKC President and Chief Executive Officer Keith Creel. “I have had the pleasure to serve and lead with John directly or indirectly for over the last two decades. His strong operating acumen and leadership capabilities has enabled him to build a strong team currently leading our CPKC Mexico Operations. As a result, the team is ready to take the reins and continue to build on the operational momentum generated since this historic combination took place last April. As leaders we are charged to leave our organizations better - John has undoubtedly impacted Kansas City Southern (KCS) and CPKC in a positive way, for which we are grateful.”

In exchange for certain considerations, CPKC has agreed to a waiver of Mr. Orr’s non-competition agreement to allow him to work for Norfolk Southern.

CPKC and Norfolk Southern have entered into an agreement in connection with the waiver of Mr. Orr’s non-competition agreement, which includes a one-time waiver fee of US$25 million plus certain operational and commercial considerations related to the Meridian Speedway and the Meridian Terminal which will expand competition and unlock additional value related to CPKC’s proposed Meridian & Bigbee Railroad (MNBR) acquisition. Norfolk Southern has also agreed to temporally limited no-hire and non-solicitation restrictions for a short list of employees of CPKC. Mr. Orr will remain subject to his non-solicitation restrictions.

Mr. Orr was appointed Executive Vice President and Chief Transformation Officer of CPKC on April 14, 2023. Prior to this role, he served as Executive Vice President Operations for Kansas City Southern from 2021 through 2023. The role of Chief Transformation Officer will not be replaced and Mr. Orr’s portfolio will be integrated into CPKC’s existing operational structure.

Forward looking information

This news release contains certain forward-looking information relating, but not limited to, anticipated benefits of the agreement with Norfolk Southern and operational and commercial considerations related to the Meridian Speedway and Meridian Terminal and the proposed MNBR acquisition.

The forward-looking information that may be in this news release is based on current expectations, estimates, projections and assumptions, having regard to CPKC’s experience and its perception of historical trends, and includes, but is not limited to, expectations, estimates, projections and assumptions relating to: changes in business strategies, North American and global economic growth and conditions; commodity demand growth; sustainable industrial and agricultural production; commodity prices and interest rates; performance of our assets and equipment; sufficiency of our budgeted capital expenditures in carrying out our business plan; geopolitical conditions, applicable laws, regulations and government policies; the availability and cost of labour, services and infrastructure; the satisfaction by third parties of their obligations to CPKC; and carbon markets, evolving sustainability strategies, and scientific or technological developments. Although CPKC believes the expectations, estimates, projections and assumptions reflected in the forward-looking information presented herein are reasonable as of the date hereof, there can be no assurance that they will prove to be correct. Current conditions, economic and otherwise, render assumptions, although reasonable when made, subject to greater uncertainty.

Undue reliance should not be placed on forward-looking information as actual results may differ materially from those expressed or implied by forward-looking information. By its nature, CPKC’s forward-looking information involves inherent risks and uncertainties that could cause actual results to differ materially from the forward looking information, including, but not limited to, the following factors: changes in business strategies and strategic opportunities; general Canadian, U.S., Mexican and global social, economic, political, credit and business conditions; risks associated with agricultural production such as weather conditions and insect populations; the availability and price of energy commodities; the effects of competition and pricing pressures, including competition from other rail carriers, trucking companies and maritime shippers in Canada, the U.S. and Mexico; North American and global economic growth and conditions; industry capacity; shifts in market demand; changes in commodity prices and commodity demand; uncertainty surrounding timing and volumes of commodities being shipped via CPKC; inflation; geopolitical instability; changes in laws, regulations and government policies, including regulation of rates; changes in taxes and tax rates; potential increases in maintenance and operating costs; changes in fuel prices; disruption in fuel supplies; uncertainties of investigations, proceedings or other types of claims and litigation; compliance with environmental regulations; labour disputes; changes in labour costs and labour difficulties; risks and liabilities arising from derailments; transportation of dangerous goods; timing of completion of capital and maintenance projects; sufficiency of budgeted capital expenditures in carrying out business plans; services and infrastructure; the satisfaction by third parties of their obligations; currency and interest rate fluctuations; exchange rates; effects of changes in market conditions and discount rates on the financial position of pension plans and investments; trade restrictions or other changes to international trade arrangements; the effects of current and future multinational trade agreements on the level of trade among Canada, the U.S. and Mexico; climate change and the market and regulatory responses to climate change; anticipated in-service dates; success of hedging activities; operational performance and reliability; customer, regulatory and other stakeholder approvals and support; regulatory and legislative decisions and actions; the adverse impact of any termination or revocation by the Mexican government of Kansas City Southern de México, S.A. de C.V.’s Concession; public opinion; various events that could disrupt operations, including severe weather, such as droughts, floods, avalanches and earthquakes, and cybersecurity attacks, as well as security threats and governmental response to them, and technological changes; acts of terrorism, war or other acts of violence or crime or risk of such activities; insurance coverage limitations; material adverse changes in economic and industry conditions, including the availability of short and long-term financing; the demand environment for logistics requirements and energy prices, restrictions imposed by public health authorities or governments, fiscal and monetary policy responses by governments and financial institutions, and disruptions to global supply chains; the realization of anticipated benefits and synergies of the CP-KCS transaction and the timing thereof; the satisfaction of the conditions imposed by the U.S. Surface Transportation Board in its March 15, 2023 final decision; the success of integration plans for KCS; other disruptions arising from the CP-KCS integration; estimated future dividends; financial strength and flexibility; debt and equity market conditions, including the ability to access capital markets on favourable terms or at all; cost of debt and equity capital; improvement in data collection and measuring systems; industry-driven changes to methodologies; and the ability of the management of CPKC to execute key priorities, including those in connection with the CP-KCS transaction. The foregoing list of factors is not exhaustive. These and other factors are detailed from time to time in reports filed by CPKC with securities regulators in Canada and the United States.

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Reference should be made to “Item 1A - Risk Factors” and “Item 7 - Management’s Discussion and Analysis of Financial Condition and Results of Operations - Forward-Looking Statements” in CPKC’s annual and interim reports on Form 10-K and 10-Q.

Any forward-looking information contained in this news release is made as of the date hereof. Except as required by law, CPKC undertakes no obligation to update publicly or otherwise revise any forward-looking information, or the foregoing assumptions and risks affecting such forward-looking information, whether as a result of new information, future events or otherwise.

About CPKC

With its global headquarters in Calgary, Alta., Canada, CPKC is the first and only single-line transnational railway linking Canada, the United States and México, with unrivaled access to major ports from Vancouver to Atlantic Canada to the Gulf of México to Lázaro Cárdenas, México. Stretching approximately 20,000 route miles and employing 20,000 railroaders, CPKC provides North American customers unparalleled rail service and network reach to key markets across the continent. CPKC is growing with its customers, offering a suite of freight transportation services, logistics solutions and supply chain expertise. Visit cpkcr.com to learn more about the rail advantages of CPKC. CP-IR

Contacts:

Media

mediarelations@cpkcr.com

Investment Community

Chris De Bruyn

403-319-3591

investor@cpkcr.com

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