---
description: Side-by-side comparison of Windward System Five vs Lightspeed Retail. Learn about each of the product's price, benefits and disadvantages. Choose the best software for your business in Singapore.
image: https://gdm-localsites-assets-gfprod.imgix.net/images/capterra/og_logo-e5a8c001ed0bd1bb922639230fcea71a.png?auto=format%2Cenhance%2Ccompress
title: Windward System Five vs Lightspeed Retail Comparison - Capterra Singapore 2026
---

Breadcrumb: [Home](/) > [Retail Management Software](/directory/20053/retail-management-systems/software) > [Windward System Five \<span\>vs\</span\> Lightspeed Retail](https://www.capterra.com.sg/compare/43189/120491/windward-system-five/vs/lightspeed-retail)

# Compare Windward System Five vs Lightspeed Retail

Canonical: https://www.capterra.com.sg/compare/43189/120491/windward-system-five/vs/lightspeed-retail

> Detailed comparison between Windward System Five and Lightspeed Retail. Check ratings, reviews, pricing, and features to make the best decision for your business.

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## At a Glance

| Metric | Windward System Five | Lightspeed Retail |
| **Overall rating** | 3.8/5 | 4.0/5 |
| **Total Reviews** | 189 | 975 |
| **Starting Price** | US$155.00 | US$109.00 |
| **Free Trial** | Yes | Yes |
| **Free Version** | No | No |
| **Deployment** | Cloud, SaaS, Web-based, Windows (Desktop), Windows (On-Premise), Linux (On-Premise) | Cloud, SaaS, Web-based, Mac (Desktop), Windows (Desktop), Linux (Desktop), Chromebook (Desktop), iPad (Mobile) |
| **Support** | Email/Help Desk, FAQs/Forum, Knowledge Base, Phone Support, 24/7 (Live rep) | Email/Help Desk, FAQs/Forum, Knowledge Base, Phone Support, 24/7 (Live rep), Chat |
| **Training** | In Person, Live Online, Webinars, Documentation, Videos | Live Online, Webinars, Documentation, Videos |

## Best for

### Windward System Five

Independent SMBs in retail, wholesale, and service businesses needing a customizable POS + inventory + accounting suite with reporting and e‑commerce integration.

### Lightspeed Retail

Lightspeed's functionalities are aligned with retailers' and restaurateurs' priorities. It simplifies day-to-day tasks so you're free to focus on what matters: business growth and customer experience

## Key features

### Windward System Five

- API
- Billing & Invoicing
- CRM
- Customer Database
- Customizable Reports
- Discount Management
- Inventory Optimization
- Inventory Replenishment
- Merchandise Management
- Ordering Automation
- Point of Sale (POS)
- Pricing Management
- Product Catalog
- Real-Time Analytics
- Real-Time Data
- Real-Time Reporting
- Returns Management
- Stock Management
- Supplier Management
- eCommerce Management

### Lightspeed Retail

- API
- Billing & Invoicing
- CRM
- Customer Database
- Customizable Reports
- Discount Management
- Inventory Optimization
- Inventory Replenishment
- Merchandise Management
- Ordering Automation
- Point of Sale (POS)
- Pricing Management
- Product Catalog
- Real-Time Analytics
- Real-Time Data
- Real-Time Reporting
- Returns Management
- Stock Management
- Supplier Management
- eCommerce Management

## Links

- [View Windward System Five Profile](https://www.capterra.com.sg/software/43189/windward-system-five)
- [View Lightspeed Retail Profile](https://www.capterra.com.sg/software/120491/lightspeed-retail)
- [View Original Comparison](https://www.capterra.com.sg/compare/43189/120491/windward-system-five/vs/lightspeed-retail)

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