console.log

$ GOOS=windows GOARCH=386 go get -u github.com/Microsoft/go-winio
$ GOOS=windows GOARCH=386 go build main.go

# 失敗のパターンは3つあって、どうやらgoroutineの実行タイミングで変わってきているようです。
# 各パターンでwineがUnhandled page faultのメッセージを出している箇所以降は、goroutineが不正終了してListenしたものが閉じられていないためだと思われます。

# クライアント側が失敗するパターン
$ wine main.exe
0009:fixme:process:SetProcessPriorityBoost (0xffffffff,1): stub
0037:fixme:file:SetFileCompletionNotificationModes 0x98 3 - stub
2018/12/06 02:34:33 Dial Error
2018/12/06 02:34:33 Accept Error
2018/12/06 02:34:33 open \\.\pipe\winiotestpipe: File not found.
wine: Unhandled page fault on read access to 0x4286e2d1 at address 0x428a070a (thread 0029), starting debugger...
0029:err:seh:start_debugger Couldn't start debugger ("winedbg --auto 32 192") (1115)
Read the Wine Developers Guide on how to set up winedbg or another debugger
0029:err:seh:raise_exception Unhandled exception code c0000005 flags 0 addr 0x939b08b5
wine client error:29: write: Bad file descriptor

# おそらくサーバ側が失敗するパターン
$ wine main.exe
0009:fixme:process:SetProcessPriorityBoost (0xffffffff,1): stub
0009:fixme:file:SetFileCompletionNotificationModes 0x88 3 - stub
2018/12/06 02:36:59 ListenPipe Error
2018/12/06 02:36:59 Dial Error
2018/12/06 02:36:59 Call not implemented.
wine: Unhandled page fault on read access to 0x42fa854c at address 0x42a1f70a (thread 002e), starting debugger...
002e:err:seh:start_debugger Couldn't start debugger ("winedbg --auto 33 184") (1115)
Read the Wine Developers Guide on how to set up winedbg or another debugger
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
002a:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!

# 両方出るパターン
$ wine main.exe
0009:fixme:process:SetProcessPriorityBoost (0xffffffff,1): stub
0034:fixme:file:SetFileCompletionNotificationModes 0x88 3 - stub
2018/12/06 02:38:40 Dial Error
2018/12/06 02:38:40 Accept Error
2018/12/06 02:38:40 open \\.\pipe\winiotestpipe: File not found.
2018/12/06 02:38:40 Call not implemented.
0029:err:hid_report:process_hid_report Device reports coming in too fast, last report not read yet!
wine: Unhandled page fault on read access to 0x42ea92d1 at address 0x4291f70a (thread 0029), starting debugger...
0029:err:seh:start_debugger Couldn't start debugger ("winedbg --auto 32 52") (1115)
Read the Wine Developers Guide on how to set up winedbg or another debugger
0029:err:seh:raise_exception Unhandled exception code c0000005 flags 0 addr 0x939b08b5
wine client error:29: write: Bad file descriptor

main.go

package main

import (
	"bufio"
	"github.com/Microsoft/go-winio"
	"github.com/pkg/errors"
	"log"
	"net"
	"time"
)

var testPipeName = `\\.\pipe\winiotestpipe`

func PipeServerProcess() {
	l, err := winio.ListenPipe(testPipeName, nil)
	if err != nil {
		log.Println("ListenPipe Error")
		log.Fatal(errors.WithStack(err))
	}
	defer l.Close()

	for {
		c, err := l.Accept()
		if err != nil {
			log.Println("Accept Error")
			log.Fatal(errors.WithStack(err))
		}

		go func(c net.Conn) {
			rw := bufio.NewReadWriter(bufio.NewReader(c), bufio.NewWriter(c))
			str, err := rw.ReadString('\n')
			if err != nil {
				log.Println("Read Error")
				log.Fatal(errors.WithStack(err))
			}
			log.Println(str)
			c.Close()
		}(c)
	}
}

func main() {
	go PipeServerProcess()

	var d = time.Duration(100 * time.Millisecond)
	p, err := winio.DialPipe(testPipeName, &d)
	if err != nil {
		log.Println("Dial Error")
		log.Fatal(errors.WithStack(err))
	}
	rw := bufio.NewReadWriter(bufio.NewReader(p), bufio.NewWriter(p))
	_, err = rw.WriteString("Hello from parent")
	if err != nil {
		log.Println("Write Error")
		log.Fatal(errors.WithStack(err))
	}
}

versions

$ go version  
go version go1.11 darwin/amd64
$ wine --version
wine-3.0.2

go-winioでのPipeの実装はこちらにあります。
https://github.com/Microsoft/go-winio/blob/master/pipe.go
DLLのコールなのであまり失敗する要素はないように思うのですが…

コンパイルと実行に使用しているmacOSは10.14（18A391）です。